Benzoyl chloride → N-(3-Hydroxy-3,3-diphenylpropyl)benzamide

HRID 596160Notes

Reaction equation

HRID 596160 reaction equation
[OH:1][C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][CH2:4][NH2:5].[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl.N1C=CC=CC=1>[C:18]([NH:5][CH2:4][CH2:3][C:2]([OH:1])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 20540392HCID 20540392, compound

Product 1

HCID 14116453N-(3-Hydroxy-3,3-diphenylpropyl)benzamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To the solution of 58.0 g of 3-hydroxy-3,3-diphenylpropylamine in 700 ml of methylene chloride and 30.5 g of pyridine, that of 37.5 g of benzoyl chloride in 300 ml of methylene chloride is added dropwise during 2 hours while stirring and cooling with an ice-bath. Stirring is continued for 1 hour at 0°-5°, the mixture washed twice with 200 ml of N hydrochloric acid, 150 ml of 5% aqueous sodium hydroxide and 25 ml of water each, dried, evaporated and the residue triturated with diethyl ether, to yield the N-benzoyl-3-hydroxy-3,3-diphenylpropylamine melting at 140°-141°.

Workup

  1. temperaturecooling with an ice-bath
  2. stirringStirring
  3. washthe mixture washed twice with 200 ml of N hydrochloric acid, 150 ml of 5% aqueous sodium hydroxide and 25 ml of water each,
  4. customdried
  5. customevaporated
  6. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-fcb98d9ccbe147d4bc3ea34c9bdb37b4
Source dataset
uspto-grants-1977_03
Patent number
US04010166

Reaction notes

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