Diisopropylethylamine → 4-Chloro-2-[(3-hydroxy-1-phenylpropyl)amino]benzonitrile

HRID 966956Notes

Reaction equation

HRID 966956 reaction equation
[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][CH2:4][OH:5].[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15](F)[CH:14]=1.C(N(CC)C(C)C)(C)C>>[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([NH:1][CH:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:3][CH2:4][OH:5])[CH:14]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 936554-Chloro-2-fluorobenzonitrileHCID 2035001-Propanol, 3-amino-3-phenyl-

Product 1

HCID 222939464-Chloro-2-[(3-hydroxy-1-phenylpropyl)amino]benzonitrileYield 59.9%

Conditions

Temperature
140 °C

Procedure

A mixture of 3-amino-3-phenyl-1-propanol (1 g, 6.6 mmol), 4-chloro-2-fluorobenzonitrile (1 g, 6.4 mmol) and N,N-diisopropylethylamine (1.2 ml, 6.9 mmol) was stirred and heated at 140° C. for 5 h. The crude reaction mixture was cooled and purified on silica gel (ether/isohexane 1:4). The product was isolated as a colourless solid (1.1 g, 58%), m.p. 88-90° C.

Workup

  1. customThe crude reaction mixture
  2. temperaturewas cooled
  3. custompurified on silica gel (ether/isohexane 1:4)

Sources & evidence

ORD record
ord-0c8983774cc34c7789d3e0302b3e4876
Source dataset
uspto-grants-2005_10
Patent number
US06953797B2

Reaction notes

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