Phenethyl bromide → Ethyl 1-phenethyl-4-(phenylamino)piperidine-4-carboxylate

HRID 1973783Notes

Reaction equation

HRID 1973783 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH:10]([C:17]1([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.CN(C)C(=O)C>O>[C:11]1([NH:10][C:17]2([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:18][CH2:19][N:20]([CH2:2][CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:21][CH2:22]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 7666Phenethyl bromideHCID 8471TriethylamineHCID 31374DimethylacetamideHCID 122981724-Piperidinecarboxylic acid, 4-(phenylamino)-, ethyl ester

Product 1

HCID 12298147Ethyl 1-phenethyl-4-(phenylamino)piperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 28.7 parts of (2-bromoethyl)benzene, 34.7 parts of ethyl 4-anilinoisonipecotate, 25 parts of N,N-diethylethanamine and 162 parts of N,N-dimethylacetamide is stirred for 2h. 30 at 75°-80° C. The reaction mixture is poured onto 1000 parts of water and the product is extracted three times with 210 parts of 1,1'-oxybisethane. The combined extracts are washed twice with 200 parts of water, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 2% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The oily residue is crystallized from 2,2'-oxybispropane, yielding ethyl 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate; mp. 65° C.

Workup

  1. customat 75°-80° C
  2. extractionthe product is extracted three times with 210 parts of 1,1'-oxybisethane
  3. washThe combined extracts are washed twice with 200 parts of water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and 2% 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-e7cbba88ffc94da59c626f577891e6ac
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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