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

HRID 1973802Notes

Reaction equation

HRID 1973802 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 4h. 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 silica gel 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 silica gel using
  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-59225f01d7c94b569e9a814b59d69817
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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