Hydrochloric Acid → alpha-[(1-Methylethylamino)methyl]-beta-(2-Methylphenoxy)Benzeneethanol, Hydrochloride

HRID 435506Notes

Reaction equation

HRID 435506 reaction equation
[OH:1][CH:2]([CH:9]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([NH:5][CH:6]([CH3:8])[CH3:7])=O.B.O1CCCC1.[ClH:30]>>[ClH:30].[CH3:8][CH:6]([NH:5][CH2:3][CH:2]([OH:1])[CH:9]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:7]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 13041342alpha-Hydroxy-beta-(2-Methylphenoxy)-N-(1-Methylethyl)Benzenepropanamide

Product 1

HCID 13041359alpha-[(1-Methylethylamino)methyl]-beta-(2-Methylphenoxy)Benzeneethanol, Hydrochloride

Procedure

This compound was prepared by reduction of α-hydroxy-N-(1-methylethyl)-β-(2-methylphenoxy)benzenepropanamide (1.8 g.) with borane-tetrahydrofuran complex (1 M solution in tetrahydrofuran, 13 ml.) and subsequent treatment with hydrochloric acid as described in Example 24. The crude product was purified by recrystallization from tetrahydrofuran. The product melted at 193°-195°, and weighed 0.75 g.

Workup

  1. customThe crude product was purified by recrystallization from tetrahydrofuran

Sources & evidence

ORD record
ord-889049da5e004582aa334f4ffc694b3d
Source dataset
uspto-grants-1983_08
Patent number
US04401832

Reaction notes

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