Methanol → 5-(4-Chlorophenyl)-2-piperidin-4-ylpyrimidine

HRID 1005893노트

반응식

HRID 1005893 반응식
ClC(OC(Cl)C)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[N:17][C:18]([CH:21]3[CH2:26][CH2:25][N:24](C)[CH2:23][CH2:22]3)=[N:19][CH:20]=2)=[CH:11][CH:10]=1.CO>ClCCCl.C(OCC)C>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[N:17][C:18]([CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[N:19][CH:20]=2)=[CH:11][CH:10]=1

참가 물질

6

반응물 3

HCID 887MethanolHCID 5213051-Chloroethyl chloroformateHCID 226466965-(4-Chlorophenyl)-2-(1-methylpiperidin-4-yl)pyrimidine

생성물 1

HCID 226466975-(4-Chlorophenyl)-2-piperidin-4-ylpyrimidine수율 76.1%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 3283Diethyl Ether용매

실험 절차

1-Chloroethyl chloroformate (0.50 ml) was added to a solution of 5-(4-chlorophenyl)-2-(1-methylpiperidin-4-yl)pyrimidine (0.170 g) in anhydrous 1,2-dichloroethane (10 ml) and the mixture heated to reflux, under a calcium chloride guard tube, for 20 h. The reaction was then cooled, treated with methanol (1.0 ml), and returned to reflux for a further hour. After cooling, the reaction was diluted with diethyl ether (20 ml) and extracted with water (20 ml), 0.2 M hydrochloric acid (10 ml) then 1% citric acid (50 ml). The combined aqueous extracts were back-extracted with diethyl ether (10 ml), basified to pH 13 with 46% aqueous sodium hydroxide and extracted with ethyl acetate (20 ml, then 2×10 ml). The combined ethyl acetate extracts were washed with water (10 ml), saturated brine (20 ml), dried (Na2SO4) and evaporated under reduced pressure to give the title compound as a white solid (0.123 g, 76%).

후처리

  1. temperaturethe mixture heated
  2. temperatureto reflux, under a calcium chloride guard tube
  3. temperatureThe reaction was then cooled
  4. temperatureto reflux for a further hour
  5. temperatureAfter cooling
  6. extractionextracted with water (20 ml), 0.2 M hydrochloric acid (10 ml)
  7. extractionThe combined aqueous extracts were back-extracted with diethyl ether (10 ml)
  8. extractionextracted with ethyl acetate (20 ml
  9. washThe combined ethyl acetate extracts were washed with water (10 ml), saturated brine (20 ml)
  10. dry with materialdried (Na2SO4)
  11. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-a942fe970b384fb3847d6885bce15860
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06787536B2

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