Diethanolamine → 3-[N,N-Bis(2-hydroxyethyl)amino]-1-{2-[4-(3,5-dimethoxyphenyl) butyl]phenoxy}-2-propanol

HRID 743192Notes

Reaction equation

[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:32]=[CH:31][CH:30]=[CH:29][C:23]=2[O:24][CH2:25][CH:26]2[CH2:28][O:27]2)[CH:13]=[C:14]([O:16][CH3:17])[CH:15]=1>O1CCCC1>[OH:4][CH2:3][CH2:2][N:1]([CH2:28][CH:26]([OH:27])[CH2:25][O:24][C:23]1[CH:29]=[CH:30][CH:31]=[CH:32][C:22]=1[CH2:21][CH2:20][CH2:19][CH2:18][C:12]1[CH:13]=[C:14]([O:16][CH3:17])[CH:15]=[C:10]([O:9][CH3:8])[CH:11]=1)[CH2:5][CH2:6][OH:7]

Participants

Conditions

Temperature: 50 °C

Procedure

530 mg of diethanolamine were added to a solution of 345 mg of 2-{2-[4-(3,5-dimethoxyphenyl)butyl]phenoxymethyl}oxirane [prepared as described in Example 11(a)] in 10 ml of tetrahydrofuran, and the resulting mixture was stirred at 50° C. for 24 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 7:1 by volume mixture of methylene chloride and methanol as the eluent, to give 333 mg of the title compound as a colorless oil.

Workup

customAt the end of this time, the solvent was removed by distillation under reduced pressure
customthe resulting residue was purified by column chromatography through silica gel
additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record: ord-3464e35a29ad48eea806da1b1c4708c7
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05556864

Reaction notes

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