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

HRID 743197Notes

Reaction equation

HRID 743197 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=1[O:15][CH2:16][CH:17]1[CH2:19][O:18]1.[CH3:24][NH:25][CH3:26]>O1CCCC1>[CH3:24][N:25]([CH3:26])[CH2:19][CH:17]([OH:18])[CH2:16][O:15][C:14]1[CH:20]=[CH:21][CH:22]=[CH:23][C:13]=1[CH2:12][CH2:11][CH2:10][CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 106388632-{2-[4-(2-Methoxyphenyl)butyl]phenoxymethyl}oxirane

Product 1

HCID 106206163-Dimethylamino-1-{2-[4-(2-methoxyphenyl)butyl]phenoxy}-2-propanolYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following a procedure similar to that described in Example 1(b), a solution of 260 mg of 2-{2-[4-(2-methoxyphenyl)butyl]phenoxymethyl}oxirane [prepared as described in step (a) above] in 10 ml of tetrahydrofuran was treated with 2 ml of 50% by volume aqueous dimethylamine and then worked up. The resulting 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 250 mg (yield 84%) of the title compound as a colorless oil.

Workup

  1. customThe resulting 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-ea9b668db30e4c3dba36561a10903e35
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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