Phenethyl bromide → 1-Propanone, 1-[4-(phenylamino)-1-(2-phenylethyl)-4-piperidinyl]-

HRID 1448300Notes

Reaction equation

HRID 1448300 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:10]1([NH:16][C:17]2([C:23](=[O:26])[CH2:24][CH3:25])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.CN(C)C(=O)C>O>[C:10]1([NH:16][C:17]2([C:23](=[O:26])[CH2:24][CH3:25])[CH2:22][CH2:21][N:20]([CH2:2][CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:19][CH2:18]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 7666Phenethyl bromideHCID 8471TriethylamineHCID 31374DimethylacetamideHCID 122982271-Propanone, 1-[4-(phenylamino)-4-piperidinyl]-

Product 1

HCID 122982221-Propanone, 1-[4-(phenylamino)-1-(2-phenylethyl)-4-piperidinyl]-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2.7 parts of (2-bromoethyl)benzene), 3.1 parts of 1-[4-(phenylamino)-4-piperidinyl]-1-propanone and 2.6 parts of N,N-diethylethanamine in 18 parts of N,N-dimethylacetamide is stirred for 4 h. 30 at 80° C. The reaction mixture is poured onto 100 parts of water and the product is extracted with benzene. The extract is washed with water, dried, filtered and evaporated. The oily residue is purified by column-chromatography over silicagel using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The oily residue is crystallized from 2,2'-oxybispropane, yielding 1-[4-(phenylamino)-1-(2-phenylethyl)-4-piperidinyl]-1-propanone; mp. 105.6° C.

Workup

  1. customat 80° C
  2. extractionthe product is extracted with benzene
  3. washThe extract is washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe oily residue is purified by column-chromatography over silicagel
  8. additiona mixture of trichloromethane and 5% of methanol as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. customThe oily residue is crystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-7adce952dc9d41adb6445f854fcf3c46
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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