Hydride → Cericlamine

HRID 1954495Notes

Reaction equation

HRID 1954495 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:15]([CH3:17])[CH3:16])([CH3:14])[C:11](O)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[H-]>C1(C)C=CC=CC=1>[CH3:14][C:10]([N:15]([CH3:17])[CH3:16])([CH2:11][OH:12])[CH2:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 3

HCID 166653HydrideHCID 11822623HCID 11822623, compoundHCID 68718528lithium aluminium hydride THF

Product 1

HCID 131074Cericlamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.65 to 1.75 mol of amino ester (II) are reduced in toluene with a lithium aluminium hydride-tetrahydrofuran addition complex prepared starting from 1 mol of hydride, to obtain (+/-)3-(3,4-dichlorophenyl)-2-dimethylamino-2-methylpropan-1-ol (I) or cericlamine which is optionally salified with hydrochloric acid.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-ea9dc6682cba42149ce621611534cef9
Source dataset
uspto-grants-2000_09
Patent number
US06121491

Reaction notes

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