Water → beta-[(2-Hydroxy-1-methylethyl)amino]-alpha-phenylbenzeneethanol

HRID 1381523Notes

Reaction equation

HRID 1381523 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C@H:7]2[O:9][C@@H:8]2[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:5][CH:6]=1.[NH2:16][CH:17]([CH3:20])[CH2:18][OH:19].O>CO>[OH:19][CH2:18][CH:17]([NH:16][CH:7]([C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[CH:8]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[OH:9])[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 51262-AminopropanolHCID 185583(R,R)-Stilbene oxide

Product 1

HCID 14391210beta-[(2-Hydroxy-1-methylethyl)amino]-alpha-phenylbenzeneethanolYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of trans-stilbene oxide (3.93 g, 0.020 mole) and 2-amino-1-propanol (4.51 g, 0.060 mole) was heated on a steam bath for 18 hours. The reaction mixture was dissolved in methanol (20 ml) and the solution poured into water (200 ml). The viscous oil which separated from the solution crystallized on standing. The solid was collected to obtain 4.29 g (79%) of material which was recrystallized from toluene to give 3.36 g of a white solid. The solid was dried in vacuo for 2 hours, m.p. 104°-105° C.

Workup

  1. temperaturewas heated on a steam bath for 18 hours
  2. customThe viscous oil which separated from the solution
  3. customcrystallized
  4. customThe solid was collected

Sources & evidence

ORD record
ord-c0fab2521406409ca20e95d161d42351
Source dataset
uspto-grants-1989_02
Patent number
US04803200

Reaction notes

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