Triethylamine → ethyl 4-{N-(4-chlorophenyl)-N-[(4-methoxyphenyl)acetyl]amino}-1-piperidinecarboxylate

HRID 236747Notes

Reaction equation

HRID 236747 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(N(CC)CC)C.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][C:36](Cl)=[O:37])=[CH:31][CH:30]=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:36](=[O:37])[CH2:35][C:32]2[CH:33]=[CH:34][C:29]([O:28][CH3:27])=[CH:30][CH:31]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27346884-Methoxyphenylacetyl chlorideHCID 2846949Ethyl 4-[(4-chlorophenyl)amino]piperidine-1-carboxylate

Product 1

HCID 23339060ethyl 4-{N-(4-chlorophenyl)-N-[(4-methoxyphenyl)acetyl]amino}-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of 15 parts of ethyl 4-[(4-chlorophenyl)amino]-1-piperidinecarboxylate, 5.4 parts of N,N-diethylethanamine and 160 parts of benzene is added dropwise 11.07 parts of 4-methoxybenzeneacetyl chloride at a temperature between 32° to 40° C. After the addition is complete, the whole is stirred and refluxed for 3 hours. The reaction mixture is cooled and filtered. The filtrate is washed successively with water, sodium hydrogen carbonate solution and water, dried, filtered and evaporated in vacuo. The oily residue is crystallized from a mixture of 56 parts of 1,1'-oxybisethane and 40 parts of hexane. The crude solid product is filtered off and recrystallized from a mixture of benzene and 1,1'-oxybisethane, yielding 3 parts of ethyl 4-{N-(4-chlorophenyl)-N-[(4-methoxyphenyl)acetyl]amino}-1-piperidinecarboxylate; mp. 137° C.

Workup

  1. additionAfter the addition
  2. temperaturerefluxed for 3 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationfiltered
  5. washThe filtrate is washed successively with water, sodium hydrogen carbonate solution and water
  6. customdried
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe oily residue is crystallized from a mixture of 56 parts of 1,1'-oxybisethane and 40 parts of hexane
  10. filtrationThe crude solid product is filtered off
  11. customrecrystallized from a mixture of benzene and 1,1'-oxybisethane

Sources & evidence

ORD record
ord-bb209cf78d684080af6b304ad6399abf
Source dataset
uspto-grants-1979_06
Patent number
US04157393

Reaction notes

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