Benzoyl chloride → 2-Benzoyloxy-3-dimethylamino-1,1-diphenylpropane

HRID 436943Notes

Reaction equation

HRID 436943 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][N:11]([CH3:28])[CH2:12][CH:13]([OH:27])[CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[C:1]([O:27][CH:13]([CH2:12][N:11]([CH3:10])[CH3:28])[CH:14]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 125491223-Dimethylamino-1,1-diphenyl-propan-2-ol

Product 1

HCID 203090682-Benzoyloxy-3-dimethylamino-1,1-diphenylpropaneYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzoyl chloride (1.49 g.) was added to 3-dimethylamino-1,1-diphenyl-propan-2-ol (2.55 g.) in dry pyridine (10 ml.) and the solution allowed to stand for 4 hours. Pyridine was removed by evaporation and the residue dissolved in dilute hydrochloric acid and ether. Basification of the acid extract and isolation through ether in the usual manner gave 2-benzoyloxy-3-dimethylamino-1,1-diphenylpropane (3.47 g., 99%), m.p. 90° - 91°.

Workup

  1. customPyridine was removed by evaporation
  2. dissolutionthe residue dissolved in dilute hydrochloric acid
  3. extractionBasification of the acid extract

Sources & evidence

ORD record
ord-5ed8e61bb0044564a82e602f9c0d1fc0
Source dataset
uspto-grants-1977_06
Patent number
US04028415

Reaction notes

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