Phenylacetyl chloride → Ethyl 4-[(4-chlorophenyl)(phenylacetyl)amino]piperidine-1-carboxylate

HRID 2049356Notes

Reaction equation

HRID 2049356 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[C:20]1([CH2:26][C:27](Cl)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:13][CH2:14]2)[C:27](=[O:28])[CH2:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7679Phenylacetyl chlorideHCID 2846949Ethyl 4-[(4-chlorophenyl)amino]piperidine-1-carboxylate

Product 1

HCID 3017393Ethyl 4-[(4-chlorophenyl)(phenylacetyl)amino]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred solution of 58 parts of ethyl 4-[(4-chlorophenyl)amino]-1-piperidinecarboxylate in 240 parts of benzene is added dropwise a solution of 46.2 parts of benzeneacetyl chloride in 80 parts of benzene at a temperature between 40°-70° C. Upon completion, the whole is stirred and refluxed for 6 h. 15. The reaction mixture is cooled and filtered. The filtrate is washed successively with water, sodium hydrogen carbonate solution and water, then dried and evaporated in vacuo. The residue is crystallized from 1,1'-oxybisethane, yielding 47 parts of ethyl 4-[N-(4-chlorophenyl)-N-(phenylacetyl)amino]-1-piperidinecarboxylate; mp. 108° C.

Workup

  1. temperaturerefluxed for 6 h
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered
  4. washThe filtrate is washed successively with water, sodium hydrogen carbonate solution and water
  5. customdried
  6. customevaporated in vacuo
  7. customThe residue is crystallized from 1,1'-oxybisethane

Sources & evidence

ORD record
ord-4d8be5fa6f7f4ac1bdbcc26050e6f7be
Source dataset
uspto-grants-1980_04
Patent number
US04197304

Reaction notes

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