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

HRID 1448319
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HRID 1448319 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-109c42dc895e4074b521c82f6a7a0349
출처 데이터셋
uspto-grants-1979_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04179569

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