Ethoxyethylamine → beta-[(2-Ethoxyethyl)amino]-alpha-phenylbenzeneethanol

HRID 1681347Notes

Reaction equation

HRID 1681347 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:18][CH2:19][CH2:20][NH2:21])[CH3:17]>>[CH2:16]([O:18][CH2:19][CH2:20][NH:21][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])[CH3:17]

Participants

3

Reactant 2

HCID 66970EthoxyethylamineHCID 185583(R,R)-Stilbene oxide

Product 1

HCID 14391209beta-[(2-Ethoxyethyl)amino]-alpha-phenylbenzeneethanolYield 80%

Conditions

Temperature
140 °C

Procedure

A mixture of trans-stilbene oxide (1.96 g, 0.010 mol) and 2-ethoxyethylamine (2.67 g, 0.030 mol) was heated at 140° C. for 6 hours. After standing at ambient temperature for 10 hours, the solidified reaction mixture was triturated with isooctane and filtered to obtain a white solid (2.28 g, 80% yield) that was recrystallized from isooctane; mp 128°-130° C.

Workup

  1. customthe solidified reaction mixture was triturated with isooctane
  2. filtrationfiltered

Sources & evidence

ORD record
ord-84ad795380e44807833aefd4db6573a8
Source dataset
uspto-grants-1992_12
Patent number
US05171753

Reaction notes

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