Triethylamine → N-(4-chlorophenyl)-N-(1-propyl-4-piperidinyl)benzeneacetamide hydrochloride

HRID 2049373Notes

Reaction equation

HRID 2049373 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.I[CH2:32][CH2:33][CH3:34]>C1C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH:18]2[CH2:23][CH2:22][N:21]([CH2:32][CH2:33][CH3:34])[CH2:20][CH2:19]2)[C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 336431-Iodopropane2×HCID 162188N-(4-Chlorophenyl)-N-4-piperidinylbenzeneacetamide

Product 1

HCID 23339041N-(4-chlorophenyl)-N-(1-propyl-4-piperidinyl)benzeneacetamide hydrochloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of 4 parts of N-(4-chlorophenyl)-N-(4-piperidinyl)benzeneacetamide and 3 parts of N,N-diethylethanamine in 200 parts of benzene are added portionwise 4 parts of 1-iodopropane and the whole is stirred and refluxed for 47 hours. Then the second portion of 4 parts of 1-iodopropane is added and stirring and refluxing is continued for another 20h.20. The reaction mixture is cooled and filtered. The filtrate is washed with water, dried and evaporated in vacuo. From the oily free base, the hydrochloride salt is prepared in the conventional manner in 1,1'-oxybisethane. The precipitated solid salt is filtered off and dried, yielding 3.5 parts of N-(4-chlorophenyl)-N-(1-propyl-4-piperidinyl)benzeneacetamide hydrochloride; mp. 233.5° C.

Workup

  1. temperaturerefluxed for 47 hours
  2. stirringstirring
  3. temperaturerefluxing
  4. temperatureThe reaction mixture is cooled
  5. filtrationfiltered
  6. washThe filtrate is washed with water
  7. customdried
  8. customevaporated in vacuo
  9. filtrationThe precipitated solid salt is filtered off
  10. customdried

Sources & evidence

ORD record
ord-4936c918da1d4f35a70e48e5bf6c8772
Source dataset
uspto-grants-1980_04
Patent number
US04197304

Reaction notes

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