Chloroacetyl chloride → N-benzyl-N-chloroacetyl-3hydroxy-3,3-diphenylpropylamine

HRID 596163Notes

Reaction equation

HRID 596163 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][C:11]([OH:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:25][CH2:26][C:27](Cl)=[O:28]>C(N(C(C)C)CC)(C)C.C(Cl)Cl>[CH2:1]([N:8]([CH2:9][CH2:10][C:11]([OH:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:27](=[O:28])[CH2:26][Cl:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 20326648N-benzyl-3-hydroxy-3,3-diphenylpropylamine

Product 1

HCID 20326654N-benzyl-N-chloroacetyl-3hydroxy-3,3-diphenylpropylamine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

To the stirred solution of 15.6 g of N-benzyl-3-hydroxy-3,3-diphenylpropylamine in 7.0 g of di-isopropylethylamine and 150 ml of methylene chloride, that of 5.88 g of chloroacetyl chloride in 50 ml of methylene chloride is added dropwise while stirring and cooling with an ice-bath. Thereupon the solution is stirred for 15 minutes at 0°-5° and washed successively with N hydrochloric acid, 10% aqueous sodium bicarbonate and finally with saturated aqueous sodium chloride. The organic layer is separated, dried, filtered and evaporated, to yield the N-benzyl-N-chloroacetyl-3-hydroxy-3,3-diphenylpropylamine showing in the I.R. spectrum a strong band at 1640 cm-1.

Workup

  1. temperaturecooling with an ice-bath
  2. stirringThereupon the solution is stirred for 15 minutes at 0°-5°
  3. washwashed successively with N hydrochloric acid, 10% aqueous sodium bicarbonate and finally with saturated aqueous sodium chloride
  4. customThe organic layer is separated
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-2253f7b6c5904e7d86c5271e4fcee3aa
Source dataset
uspto-grants-1977_03
Patent number
US04010166

Reaction notes

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