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

HRID 1448320Notes

Reaction equation

HRID 1448320 reaction equation
[C:1]1([NH:7][C:8]2([C:22]([O:24][CH3:25])=[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:26]1([C:29]([Cl:31])=[O:30])[CH2:28][CH2:27]1.C(N(CC)CC)C>CC1C=CC=CC=1>[ClH:31].[CH:26]1([C:29]([N:7]([C:8]2([C:22]([O:24][CH3:25])=[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:30])[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 12298146Methyl 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate

Product 1

HCID 12297994methyl 4-[N-(cyclopropylcarbonyl)-N-phenylamino]-1-(2-phenylethyl)-4-piperidinecarboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5.1 parts of methyl 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate, 1.9 parts of cyclopropanecarbonyl chloride, 2.7 parts of N,N-diethylethanamine and 67.5 parts of methylbenzene is stirred and refluxed overnight. The reaction mixture is cooled to room temperature and poured onto water. The product is extracted with methylbenzene. The extract is washed with water, dried, filtered and evaporated. The oily residue is purified by column-chromatography over silicagel using a mixture of trichloromethane and 3% of methanol as eluent. The pure fractions are collected and the eluent 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 methyl 4-[N-(cyclopropylcarbonyl)-N-phenylamino]-1-(2-phenylethyl)-4-piperidinecarboxylate hydrochloride; mp. 197.8° C.

Workup

  1. temperaturerefluxed overnight
  2. additionpoured onto water
  3. extractionThe product is extracted with methylbenzene
  4. washThe extract is washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe oily residue is purified by column-chromatography over silicagel
  9. additiona mixture of trichloromethane and 3% of methanol as eluent
  10. customThe pure fractions are collected
  11. customthe eluent is evaporated
  12. filtrationThe salt is filtered off
  13. customcrystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-eeaf38d4c1d6485f9da288a76b97756f
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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