Water → beta-[[3-(2-Methylpropoxy)propyl]amino]-alpha-phenylbenzeneethanol

HRID 1381528Notes

Reaction equation

HRID 1381528 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.[CH2:16]([O:20][CH2:21][CH2:22][CH2:23][NH2:24])[CH:17]([CH3:19])[CH3:18].O>CC(C)=O>[CH3:18][CH:17]([CH3:19])[CH2:16][O:20][CH2:21][CH2:22][CH2:23][NH:24][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]

Participants

5

Reactant 3

HCID 962WaterHCID 986683-IsobutoxypropylamineHCID 185583(R,R)-Stilbene oxide

Product 1

HCID 14391212beta-[[3-(2-Methylpropoxy)propyl]amino]-alpha-phenylbenzeneethanolYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of trans-stilbene oxide (91.96 g, 0.10 mole) and 3-isobutoxy-1-propylamine (3.93 g, 0.030 mole) was heated at 140° C. for 5 hrs. After standing at ambient temperature for 18 hrs the mixture was dissolved in acetone (20 ml) and the solution poured into water (120 ml). A solid formed rapidly which was collected by filtration and dried under ambient conditions to obtain 2.89 g (88%) of the desired product. Recrystallization from tolueneisooctone gave 2.44 g of an off-white solid, m.p. 90°-92° C.

Workup

  1. customA solid formed rapidly which
  2. filtrationwas collected by filtration
  3. customdried under ambient conditions

Sources & evidence

ORD record
ord-6b0c25d5ccd64d4098acf6c0250b02c2
Source dataset
uspto-grants-1989_02
Patent number
US04803200

Reaction notes

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