Hydrochloric Acid → N-Methyl-γ-phenoxybenzenepropanamine

HRID 2225047Notes

Reaction equation

HRID 2225047 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH:5]([OH:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl>>[CH3:1][NH:2][CH2:3][CH2:4][CH:5]([O:12][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 27339893-Methylamino-1-phenylpropanol

Product 1

HCID 15894873N-Methyl-γ-phenoxybenzenepropanamine

Procedure

Under stirring, while maintaining the temperature between about 15° and about 25° C. with an ice-water bath, 12.3 g of 36 percent aqueous hydrogen chloride are dropped on the filtered organic phase, resulting in the crystallization of D-ATM hydrochloride (mw 277.80). The resulting suspension is stirred at about 20° C. for 1 hour, the solid is collected by filtration, washed twice with 40 ml of n-butyl acetate, and dried for 18 hours under vacuum at about 50° to about 60° C., yielding 32.7 g of product, a 48 percent yield based on the N-methyl-3-hydroxy-3-phenylpropylamine starting material, having a melting point of about 170° to about 174° C. The D-ATM HCl is found by chiral HPLC to be a mixture of enantiomers, with a relative ratio of 69:31.

Workup

  1. additiona mixture of enantiomers

Sources & evidence

ORD record
ord-d2bcdc1437694ff090362573a4757507
Source dataset
uspto-grants-2008_05
Patent number
US07378553B2

Reaction notes

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