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

HRID 1005893ノート

反応式

HRID 1005893 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 226466975-(4-Chlorophenyl)-2-piperidin-4-ylpyrimidine収率 76.1%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 3283Diethyl Ether溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-a942fe970b384fb3847d6885bce15860
出典データセット
uspto-grants-2004_09
特許番号
US06787536B2

反応ノート

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