N-ethyl(or -methyl or -phenyl)-N-2-halogenoethyl-1(or -2)-naphthylmethylamines. Part II. Chemical reactivity and pharmacological activity

Champman, N. B.; James, J. W.

doi:10.1039/jr9540002103

Cited by 18 publications

(7 citation statements)

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“…(1962), quoted in ref. 6, p. 120; (d) J. Seibl and T. Gáumann, Z. Anal. Chem., 197, 33 (1963); (e) D. H. Williams, H. Budzikiewicz, and C. Djerassi, J.…”

mentioning

confidence: 99%

Mass Spectrometry in Structural and Stereochemical Problems. LXV.¹ Synthesis and Fragmentation Behavior of 15-Keto Steroids. The Importance of Interatomic Distance in the McLafferty Rearrangement²

Djerassi¹,

Mutzenbecher²,

Fajkoš³

et al. 1965

J. Am. Chem. Soc.

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“…(1962), quoted in ref. 6, p. 120; (d) J. Seibl and T. Gáumann, Z. Anal. Chem., 197, 33 (1963); (e) D. H. Williams, H. Budzikiewicz, and C. Djerassi, J.…”

mentioning

confidence: 99%

Mass Spectrometry in Structural and Stereochemical Problems. LXV.¹ Synthesis and Fragmentation Behavior of 15-Keto Steroids. The Importance of Interatomic Distance in the McLafferty Rearrangement²

Djerassi¹,

Mutzenbecher²,

Fajkoš³

et al. 1965

J. Am. Chem. Soc.

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“…[7][8][9][10][11] In the past, reliance has been placed upon bulky anions, such as picrylsulfonate,12-16 to provide low solubility and thereby permit the trapping of aziridinium intermediates. Since kinetic studies have clearly shown the accumulation of aziridinium ions from /3-chloroethylamines prior to dimerization, hydrolysis, and displacement,16-19 we decided to try to trap these cations with perchlorate anion, the choice being directed by our previous favorable experience with the isolation of stable aziridinium perchlorates.1 •4-6 In a previous paper we described the conversions of two special 0-bromoethylamines, 13-bromomethyl-lazatricyclo [4.3.2.0.1 •1305•13]tetradecane and N-(l-bromocyclohexylmethyl)pyrrolidine, to the respective aziridinium perchlorates, 1-azoniatetracyclo [7.3.2. -0. i.1306 •13 ]tetradecane perchlorate and 5-azoniadispiro-[4.0.5.1 Jdodecane perchlorate.…”

mentioning

confidence: 99%

Small Charged Rings. VII. Interconversion of Substituted β-Chloroethylamines and Aziridinium Salts^1-3

Leonard¹,

Paukstelis²

1965

J. Org. Chem.

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Small Charged Rings. VII 821 was no longer present. The bulk of the reaction mixture was added dropwise with stirring to 100 ml. of anhydrous ether. The colorless solid was washed with ether: 0.62 g. (95%), identical with earlier preparations of 3-benzyl-2-methyl-l,3-diazaspiro-[4.5]dec-l-ene perchlorate.G.-A glass rod was dipped into 72% aqueous perchloric acid, shaken free of adhering drops of acid and then dripped into a suspension of 0.100 g. (0.27 mmole) of 3-benzyl-3-ethyl-2-methyl-laza-3-azoniaspiro[4.5]dec-1 -ene perchlorate in 10 ml. of water. The mixture was warmed on a steam bath until solution was complete (ca. 3 min., maximum temperature of mixture 78°), cooled, and extracted with four 5-ml. portions of ether. Evaporation of the aqueous solution gave 0.070 g. (92%) of solid product identical with other samples of 3-ethyl-2-methyl-l ,3-diazaspiro[4.51dec-1-ene perchlorate. The ether extract was dried (Na2S04), and concentration gave a few drops of an oil which on vapor phase chromatography (silicone rubber column, 175°) gave a single peak identical in retention time with that of benzyl alcohol under the same conditions. l-Benzyl-3-ethyl-2-methyl-3-aza-l-azoniaspiro[4.5]dec-l-ene Perchlorate (IV).-To a stirred suspension of 0.73 g. (2.6 mmoles) of 3-ethyl-2-methyl-l ,3-diazaspiro [4.5] dec-1 -ene perchlorate in 10 ml. of water were added 2.8 ml. of 1 N sodium hydroxide solution and 10 ml. of ether. The mixture was stirred for 15 min. and separated; the aqueous phase was further extracted with four 5-ml. portions of ether. The combined ether solution was dried (MgSÓ4) and treated with 0.321 ml. (462 mg.; 2.7 mmoles) of benzyl bromide. The sirupy residue (0.58 g.) resulting from evaporation of the solvent could not be made to crystallize: si¡« 1610 and 1555 cm.-1. A solution of the sirup in 17 ml. of methanol was treated with 344 mg. (1.66 mmoles) of silver perchlorate in 10 ml. of methanol. Filtration afforded 301 mg.(96%) of silver bromide. The methanol solution was concentrated and treated with ether. The sticky solid was recrystallized from ethyl acetate: 0.51 g. (83%); m.p. 120-121°; v™ 1615 and 1560 cm.-1; n.m.r.-values (CDC13, TMS) 2.66 (5H, aromatic protons), 5.31 (s, 2H, benzyl CH2), 6.16 (s, 2H, imidazolinium CH2), 6.34 (?,«/ = 7 c.p.s., 2H, CH2CH3), 7.77 (s 3H, 2-CH3), 7.9-8.9 (unresolved m, 10H, cyclohexane protons), and 8.67 p.p.m. (t, 3H, CH2CH3).

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“…; the aziridinium ion XIII from the N-CH3 singlet at = 3.17 p.p.m. ; and the piperazinium ion XIV from the ring methylenes at Although Bartlett,et al,6 attempted to use the thiosulfate titration technique for estimation of the aziridinium ion concentrations in their studies of this compound, the rate of reaction with the ring was too slow to be useful. The n.m.r.…”

Section: Resultsmentioning

confidence: 99%

A Nuclear Magnetic Resonance Study of the 2-Haloethylamines

Levins¹,

Papanastassiou²

1965

J. Am. Chem. Soc.

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N-ethyl(or -methyl or -phenyl)-N-2-halogenoethyl-1(or -2)-naphthylmethylamines. Part II. Chemical reactivity and pharmacological activity

Abstract: Halogenoethyl-1 (OY -2)-na~hthylmethyZamines. Part I I . 2103 N-Ethyl (or -Methyl or -PhenyZ) -N-Z-haZogenoethyl-1 (or -2) -naphthylmethylarnines. Part II. * Chemical Reactivity and Pharmacological Activity.

Cited by 18 publications

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Mass Spectrometry in Structural and Stereochemical Problems. LXV.¹ Synthesis and Fragmentation Behavior of 15-Keto Steroids. The Importance of Interatomic Distance in the McLafferty Rearrangement²

Mass Spectrometry in Structural and Stereochemical Problems. LXV.¹ Synthesis and Fragmentation Behavior of 15-Keto Steroids. The Importance of Interatomic Distance in the McLafferty Rearrangement²

Small Charged Rings. VII. Interconversion of Substituted β-Chloroethylamines and Aziridinium Salts^1-3

A Nuclear Magnetic Resonance Study of the 2-Haloethylamines

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N-ethyl(or -methyl or -phenyl)-N-2-halogenoethyl-1(or -2)-naphthylmethylamines. Part II. Chemical reactivity and pharmacological activity

Abstract: Halogenoethyl-1 (OY -2)-na~hthylmethyZamines. Part I I . 2103 N-Ethyl (or -Methyl or -PhenyZ) -N-Z-haZogenoethyl-1 (or -2) -naphthylmethylarnines. Part II. * Chemical Reactivity and Pharmacological Activity.

Cited by 18 publications

References 0 publications

Mass Spectrometry in Structural and Stereochemical Problems. LXV.1 Synthesis and Fragmentation Behavior of 15-Keto Steroids. The Importance of Interatomic Distance in the McLafferty Rearrangement2

Mass Spectrometry in Structural and Stereochemical Problems. LXV.1 Synthesis and Fragmentation Behavior of 15-Keto Steroids. The Importance of Interatomic Distance in the McLafferty Rearrangement2

Small Charged Rings. VII. Interconversion of Substituted β-Chloroethylamines and Aziridinium Salts1-3

A Nuclear Magnetic Resonance Study of the 2-Haloethylamines

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Mass Spectrometry in Structural and Stereochemical Problems. LXV.¹ Synthesis and Fragmentation Behavior of 15-Keto Steroids. The Importance of Interatomic Distance in the McLafferty Rearrangement²

Mass Spectrometry in Structural and Stereochemical Problems. LXV.¹ Synthesis and Fragmentation Behavior of 15-Keto Steroids. The Importance of Interatomic Distance in the McLafferty Rearrangement²

Small Charged Rings. VII. Interconversion of Substituted β-Chloroethylamines and Aziridinium Salts^1-3