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Water → N-(1-cyclopentyl-4-piperidinyl)-3-methyl-N-(2-pyrimidinyl)benzeneacetamide ethanedioate

HRID 2049374
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HRID 2049374 반응식
[CH:1]1([N:6]2[CH2:11][CH2:10][CH:9]([NH:12][C:13]3[N:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:19][C:20]1[CH:21]=[C:22]([CH2:26][C:27](Cl)=[O:28])[CH:23]=[CH:24][CH:25]=1.[C:30](=[O:33])([O-:32])[O-].[Na+].[Na+].CC1C=CC=CC=1C.[OH2:44]>>[C:27]([OH:28])(=[O:44])[C:30]([OH:32])=[O:33].[CH:1]1([N:6]2[CH2:11][CH2:10][CH:9]([N:12]([C:13]3[N:14]=[CH:15][CH:16]=[CH:17][N:18]=3)[C:27](=[O:28])[CH2:26][C:22]3[CH:23]=[CH:24][CH:25]=[C:20]([CH3:19])[CH:21]=3)[CH2:8][CH2:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 5

HCID 962WaterHCID 7237O-XyleneHCID 10340Sodium CarbonateHCID 2760633m-Tolylacetyl chloride2회HCID 23339052HCID 23339052, 화합물

생성물 1

HCID 86736170N-(1-cyclopentyl-4-piperidinyl)-3-methyl-N-(2-pyrimidinyl)benzeneacetamide ethanedioate

실험 절차

A mixture of 4.5 parts of N-(1-cyclopentyl-4-piperidinyl)-2-pyrimidinamine, 3.4 parts of 3-methylbenzeneacetyl chloride, 2 parts of sodium carbonate and 180 parts of dimethylbenzene is stirred and refluxed for 17 hours. Another 9 parts of 3-methylbenzeneacetyl chloride is added dropwise. Upon completion, stirring is continued for 67 hours at reflux temperature. The reaction mixture is cooled, water is added and the layers are separated. The organic phase is extracted with a diluted hydrochloric acid solution. The combined aqueous phases are washed with benzene and alkalized with a diluted sodium hydroxide solution while cooling in an ice-bath. The product is extracted twice with trichloromethane. The combined extracts are dried, filtered and evaporated. The residue is converted into the ethanedioate salt in 2-propanol. The salt is filtered off and crystallized twice: first from ethanol and then from methanol, yielding 1 part of N-(1-cyclopentyl-4-piperidinyl)-3-methyl-N-(2-pyrimidinyl)benzeneacetamide ethanedioate; mp. 204.1° C.

후처리

  1. temperaturerefluxed for 17 hours
  2. stirringUpon completion, stirring
  3. temperatureat reflux temperature
  4. temperatureThe reaction mixture is cooled
  5. customthe layers are separated
  6. extractionThe organic phase is extracted with a diluted hydrochloric acid solution
  7. washThe combined aqueous phases are washed with benzene
  8. temperaturewhile cooling in an ice-bath
  9. extractionThe product is extracted twice with trichloromethane
  10. customThe combined extracts are dried
  11. filtrationfiltered
  12. customevaporated
  13. filtrationThe salt is filtered off
  14. customcrystallized twice

출처 및 근거

ORD 기록
ord-7ca10ca066134d8eb45707420c3938dd
출처 데이터셋
uspto-grants-1980_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04197304

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