Potassium Carbonate → Benzyl 1-(2,6-dimethylpyrimidin-4-yl)piperidin-4-yl(methyl)carbamate

HRID 1193319ノート

反応式

HRID 1193319 の反応式
[CH3:1][N:2]([CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[C:3](=[O:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[C:20]1[CH:25]=[C:24]([CH3:26])[N:23]=[C:22]([CH3:27])[N:21]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:27][C:22]1[N:21]=[C:20]([N:16]2[CH2:15][CH2:14][CH:13]([N:2]([CH3:1])[C:3](=[O:12])[O:4][CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:18][CH2:17]2)[CH:25]=[C:24]([CH3:26])[N:23]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 31541994-Chloro-2,6-dimethylpyrimidineHCID 18677746Benzyl methyl(piperidin-4-yl)carbamate

生成物 1

HCID 66798782Benzyl 1-(2,6-dimethylpyrimidin-4-yl)piperidin-4-yl(methyl)carbamate収率 62%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of benzyl methyl(piperidin-4-yl)carbamate (stage 3 AMN-52) (17.24 mmol, 1.0 eq.), 4-chloro-2,6-dimethylpyrimidine (2.94 g, 2068 mmol, 1.2 eq.) and K2CO3 (4.76 g, 34.48 mmol, 2.0 eq.) in acetone (80 ml) was refluxed for 14 hours. The mixture was concentrated, and the residue was taken up in water (150 ml) and extracted with ethyl acetate (2×200 ml). The combined organic phases were washed with water (150 ml) and sat. NaCl solution (150 ml), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 70% ethyl acetate/hexane). Yield: 62% (3.8 g, 10.73 mmol)

後処理

  1. temperaturewas refluxed for 14 hours
  2. concentrationThe mixture was concentrated
  3. extractionextracted with ethyl acetate (2×200 ml)
  4. washThe combined organic phases were washed with water (150 ml) and sat. NaCl solution (150 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography (silica gel, 70% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-ef9fa45e3d4b449eb50e458b1d2699e4
出典データセット
uspto-grants-2014_03
特許番号
US08680159B2

反応ノート

読み込み中…