Phenethyl bromide → 4-(4-Methylanilino)-1-(2-phenylethyl)piperidine-4-carboxamide

HRID 1973809Notes

Reaction equation

HRID 1973809 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2([C:24]([NH2:26])=[O:25])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:13][CH:12]=1.C(N(CC)CC)C>CN(C)C(=O)C>[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2([C:24]([NH2:26])=[O:25])[CH2:19][CH2:20][N:21]([CH2:2][CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:22][CH2:23]2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 8471TriethylamineHCID 4172394-Piperidinecarboxamide, 4-[(4-methylphenyl)amino]-

Product 1

HCID 203821914-(4-Methylanilino)-1-(2-phenylethyl)piperidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 33.35 parts of (2-bromoethyl)benzene, 35 parts of 4-[N-(4-methylphenyl)amino]-4-piperidinecarboxamide, 20 parts of N,N-diethylethanamine and 225 parts of N,N-dimethylacetamide is stirred for 4 hours at 70°-80° C. The reaction mixture is poured onto water and the product is extracted with trichloromethane. The extract is washed with water, dried, filtered and evaporated. The oily residue is poured onto water, whereupon the product is precipitated. It is filtered off and suspended twice in water. The product is filtered off again, washed with 2,2'-oxybispropane and dried, yielding 4-[N-(4-methylphenyl)amino]-1-(2-phenylethyl)-4-piperidinecarboxamide; mp. 163.1° C.

Workup

  1. additionThe reaction mixture is poured onto water
  2. extractionthe product is extracted with trichloromethane
  3. washThe extract is washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. additionThe oily residue is poured onto water, whereupon the product
  8. customis precipitated
  9. filtrationIt is filtered off
  10. filtrationThe product is filtered off again
  11. washwashed with 2,2'-oxybispropane
  12. customdried

Sources & evidence

ORD record
ord-2971d27e840949f085a11b8a15582bb3
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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