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Water → N-[3-(4-Hydroxymethylphenyl)-1-methylpropyl]-2-hydroxy-2-(3-trifluoromethylphenyl)ethanamine

HRID 434365
Notes
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Reaction equation

HRID 434365 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH:13]([NH:15][CH2:16][CH:17]([OH:28])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[CH3:14])=[CH:7][CH:6]=1)(OC)=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[OH:2][CH2:1][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][CH:13]([NH:15][CH2:16][CH:17]([OH:28])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:27])[F:25])[CH:19]=2)[CH3:14])=[CH:9][CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 20493837N-(3-(4-Carbomethoxyphenyl)-1-methylpropyl)-2-hydroxy-2-(3-trifluoromethylphenyl)ethanamineHCID 21226445Aluminium lithium hydride

Product 1

HCID 20493825N-[3-(4-Hydroxymethylphenyl)-1-methylpropyl]-2-hydroxy-2-(3-trifluoromethylphenyl)ethanamine

Reagents, catalysts & solvents

1
HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of N-[3-(4-carbomethoxyphenyl)-1-methylpropyl]-2-hydroxy-2-(3-trifluoromethylphenyl) ethanamine (2.5 g) in dry ether (50 ml) was added to a suspension of lithium aluminium hydride (0.88 g) in dry ether (100 ml) under an atmosphere of nitrogen and the resulting mixture was boiled for 1 hour before being cooled and treated with water (0.9 ml); 2 N NaOH (1.8 ml) then water (2.7 ml) and stirred for a further hour.

Workup

  1. temperaturebefore being cooled

Sources & evidence

ORD record
ord-41e2001f98024a149d58d09d3c2728a7
Source dataset
uspto-grants-1983_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04396627

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes