t-Carbinamines, RR'R”CNH<sub>2</sub>. I. Reaction with Alkyl Halides and Alkylene Oxides<sup>1</sup>

Bortnick, Newman M.; Luskin, Leo S.; Hurwitz, Melvin D.; Craig, W. E.; Exner, Lawrence J.; Mirza, Jean

doi:10.1021/ja01597a048

Cited by 33 publications

(7 citation statements)

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“…spectroscopy. The amine disappeared totally in less than 1 min, and was being replaced by a salt in which the two ethyl groups were nonequivalent (CH 2 groups were apparent sextets at d 4.28 and 4.88), as might be expected with the presence of a chiral carbon as in (21), and the hydrogens within each CH 2 group were also non-equivalent. The alternative ammonium salt, equivalent to (2), would be unlikely to show such striking non-equivalence in the ethyl groups, as rotation around carbon-nitrogen bonds is not significantly restricted.…”

Section: Resultsmentioning

confidence: 92%

Phenyl Chloro(thionoformate): a New Dealkylating Agent of Tertiary Amines

Millan

Prager²

1999

Aust. J. Chem.

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Phenyl chloro(thionoformate) reacts rapidly with unhindered tertiary aliphatic amines at 20° to give a thiocarbamate and an alkyl chloride. Dialkylcyclohexylamines react surprisingly rapidly to form predominantly cyclohexene. The thiocarbamates are converted into the secondary amine salt by treatment with dimethyl sulfate, followed by hydrolysis with water. Rates of reaction and alkyl group cleavage selectivity in amines were found to be superior or comparable to those previously reported with chloroformates.

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Section: Resultsmentioning

confidence: 92%

Phenyl Chloro(thionoformate): a New Dealkylating Agent of Tertiary Amines

Millan

Prager²

1999

Aust. J. Chem.

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“…Moreover, guanidyl substitution at the end of the side chain and introduction of an ester group between the aromatic ring and the side chain were also made, expecting new hypotensives. Among these compounds, compounds 5 and 6 have been briefly reported to inhibit the hypertensive effects of noradrenaline and tyramine.2 Two of the present authors have already claimed compounds (9)(10)(11) as /3-blocking agents in Japanese Patents. 3 Chemistry.…”

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confidence: 85%

Synthesis and adrenergic .beta.-blocking activity of some 1,3-benzodioxole derivatives

Tatsuno¹,

Goto²,

Shigenobu³

et al. 1977

J. Med. Chem.

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A series of 1,3-benzodioxole derivatives was synthesized. We found four compounds (2,3,10 and 11 in Table IV) to have about the same order of beta-blocking activity as that of sotalol. In addition, it is of interest that some of the compounds (2-4) were found to have hypotensive activites, although they were about one-tenth of that of hydralazine. Sotalol did not produce any change in blood pressure, and propranolol raised the blood pressure.

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“…t-Butylethylamine is not commercially available, and has been prepared previously in 50% yield from t-butylamine and eLkAyl bromide. 7 The material prepared in this manner was contaminated with t-butylamine which could not be removed by distillation. The presence of We have developed procedures to synthesize TMP on the multi-kg sca!e from inexpensive phorone and ammonium hydroxide followed by Wolff-Kischner reduction.…”

Section: Hooc Cicomentioning

confidence: 99%