Triethylamine → ethyl 4-[N-(cyclopropylcarbonyl)-N-phenylamino]-1-(2-phenylethyl)-4-piperidinecarboxylate hydrochloride

HRID 1448319Notes

Reaction equation

HRID 1448319 reaction equation
[C:1]1([NH:7][C:8]2([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:27]1([C:30]([Cl:32])=[O:31])[CH2:29][CH2:28]1.C(N(CC)CC)C>CC1C=CC=CC=1>[ClH:32].[CH:27]1([C:30]([N:7]([C:8]2([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:12][CH2:13]2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:31])[CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 12298147Ethyl 1-phenethyl-4-(phenylamino)piperidine-4-carboxylate

Product 1

HCID 12298000ethyl 4-[N-(cyclopropylcarbonyl)-N-phenylamino]-1-(2-phenylethyl)-4-piperidinecarboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3.52 parts of ethyl 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate, 1.25 parts of cyclopropanecarbonyl chloride, 1.8 parts of N,N-diethylethanamine and 45 parts of methylbenzene is stirred and refluxed overnight. The reaction mixture is cooled to room temperature and washed with water. The organic phase is separated, dried, filtered and evaporated. The oily residue is dissolved in 2,2'-oxybispropane and the solution is stirred with activated charcoal. The latter is filtered off and the filtrate is evaporated. The oily residue is converted into the hydrochloride salt in 2,2'-oxybispropane and 2-propanol. The salt is filtered off and crystallized from 4-methyl-2-pentanone, yielding ethyl 4-[N-(cyclopropylcarbonyl)-N-phenylamino]-1-(2-phenylethyl)-4-piperidinecarboxylate hydrochloride; mp. 194.8° C.

Workup

  1. temperaturerefluxed overnight
  2. washwashed with water
  3. customThe organic phase is separated
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe oily residue is dissolved in 2,2'-oxybispropane
  8. stirringthe solution is stirred with activated charcoal
  9. filtrationThe latter is filtered off
  10. customthe filtrate is evaporated
  11. filtrationThe salt is filtered off
  12. customcrystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-109c42dc895e4074b521c82f6a7a0349
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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