Diphenylethylamines. I. The Preparation of Tertiary Amines by the Grignard Reaction^1,2

Test purchase, synthesis, and characterization of 2‐methoxydiphenidine (MXP) and differentiation from its meta‐ and para‐substituted isomers

“…Melting point of hydrochloride salt: 93.0–94.0 °C (methanol/Et 2 O) (lit. 132 – 135 °C (toluene)). HR‐ESIMS: observed m / z 296.2004 (theory [M + H] + : C 20 H 26 NO + m / z 296.2009).…”

Preparation and characterization of the ‘research chemical’ diphenidine, its pyrrolidine analogue, and their 2,2‐diphenylethyl isomers

“…As the salt was semi-soluble in acetone, the crystals were washed three times with a 50:50 mixture of EtOAc and diethyl ether (Et 2 O). The crystals were dried and crystallized at [21] 158 °C, [22] 207−208.5 °C, [22] 207−209 °C, [22] 207−209 °C (HCl × H 2 O, [14] 207 °C [20] ). 1 …”

“…The crystals were dried and crystallized at 0°C from methanol and Et 2 O. Melting point: 209-210.5°C with some sublimation (lit. : 120°C, [21] 158°C, [22] 207-208.5°C, [22] 207-209°C , [22] 207-209°C (HCl × H 2 O), [14] 207°C [20] ). 1 This diphenidine isomer was prepared following the same procedure using 2,2-diphenylethanamine (1.2 g, 6.08 mmol).…”

The Oxazolidines.

“…As-3j3,17/3-Dihydroxy-17a-aminoethyl- condenses with acetone when the compounds are refluxed together (62). The best and most common method, however, is azeotropic distillation, in which benzene is used as the water-entraining agent (18,19,24,28,34,35,44,(56)(57)(58)(59)92, 106, 120); occasionally, toluene or xylene has been proposed for this purpose (92,120). The condensation reactions, especially with complex ketones, are often accelerated by a trace of iodine (7,18,120), a method which has proven useful in a number of similar reactions (12,115).…”

“…It gives a product which may be 3-carbopropoxyoxazolidine (I), although its discoverers had originally assigned to it the formula (II) of N-carbopropoxy-N-methylaminoacetaldehyde. An The comparative ease with which different aminoalcohols and different car- Ci.......... Ethanolamine (7,8,9,10,11,13,14,18,28,35,75,76,85,87,88,89,108) Cl.......... N-Methylethanolamine (14,IS,19,53,74,75) l-Amino-2-propanoI (34) 2-Amino-l-propanol (58) 1-Amino-2,3-propanediol (20,83) 2-Amino-l, 3-propanediol (100) l-Amino-3-chloro-2-hydroxypropane (22,23,103) C........... Diethanolamine (19,56) jV-Ethvlethanolamine (38,66) 2-Amino-2-methvl-l-propanol (58,105) 2-Amino-l-butanol (8, 58, 88s) 2-Amino-2-methvl-l, 3-propanediol Aminotrimethy lolmethane (1,34,59,106) (1, 91, 92, 106) Ci.......... l-Amino-3-methyl-2-butanol…”