Dimethylamine → 1-{2-[4-(3-Chlorophenyl)butyl]phenoxy}-3-dimethylamino-2-propanol

HRID 743223Notes

Reaction equation

HRID 743223 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=2[O:14][CH2:15][CH:16]2[CH2:18][O:17]2)[CH:5]=[CH:6][CH:7]=1.[CH3:23][NH:24][CH3:25]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=2[O:14][CH2:15][CH:16]([OH:17])[CH2:18][N:24]([CH3:25])[CH3:23])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 105434832-{2-[4-(3-Chlorophenyl)butyl]phenoxymethyl}-oxirane

Product 1

HCID 107633821-{2-[4-(3-Chlorophenyl)butyl]phenoxy}-3-dimethylamino-2-propanolYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following a procedure similar to that described in Example 1(b), 840 mg of 2-{2-[4-(3-chlorophenyl)butyl]phenoxy methyl]oxirane [prepared as described in step (a) above] dissolved in 20 ml of tetrahydrofuran were treated with 4 ml of 50% by volume aqueous dimethylamine. The crude product was purified by column chromatography through silica gel, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, to give 789 mg (yield 82%) of the title compound as a colorless oil.

Workup

  1. customThe crude product was purified by column chromatography through silica gel
  2. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-bf2b5629d3b4449f9357d04f10ccdcfc
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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