Sodium hydride → N,N-Dimethyl-2-[2-(4-phenylbutyl)phenoxy]ethylamine

HRID 743174Notes

Reaction equation

HRID 743174 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl.[CH3:21][N:22]([CH2:24][CH2:25]Cl)[CH3:23]>CC(N(C)C)=O>[CH3:21][N:22]([CH2:24][CH2:25][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH3:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 125964892-(4-Phenylbutyl)phenol

Product 1

HCID 15389029N,N-Dimethyl-2-[2-(4-phenylbutyl)phenoxy]ethylamineYield 77.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following a procedure similar to that described in Example 2, 226 mg of 2-(4-phenylbutyl)phenol (prepared as described in Preparation 3), 96 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) and 173 mg of dimethylaminoethyl chloride hydrochloride were reacted in dimethylacetamide. The crude product extracted was purified by column chromatography through silica gel, using a 20:1 by volume mixture of methylene chloride and methanol as the eluent, to give 230 mg (yield 77%) of the title compound as an oil.

Workup

  1. extractionThe crude product extracted
  2. customwas purified by column chromatography through silica gel
  3. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-c8eaf71565e748349abcaf59b4e1dbb4
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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