Acetic Acid → 4-Benzyloxycarbonyl-1-[1-(4-pyridyl)-4-piperidinylamino]-2-piperazinone

HRID 2086234ノート

反応式

HRID 2086234 の反応式
[NH2:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][C:3]1=[O:18].[N:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]2)=[CH:21][CH:20]=1.C(O)(=O)C.[Na]>C(O)C.CO>[CH2:11]([O:10][C:8]([N:5]1[CH2:6][CH2:7][N:2]([NH:1][CH:28]2[CH2:27][CH2:26][N:25]([C:22]3[CH:23]=[CH:24][N:19]=[CH:20][CH:21]=3)[CH2:30][CH2:29]2)[C:3](=[O:18])[CH2:4]1)=[O:9])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 5360545SodiumHCID 113327931-(Pyridin-4-yl)piperidin-4-oneHCID 22727156Benzyl 4-amino-3-oxopiperazine-1-carboxylate

生成物 1

HCID 178254544-Benzyloxycarbonyl-1-[1-(4-pyridyl)-4-piperidinylamino]-2-piperazinone収率 70.2%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

A solution of 1-amino-4-benzyloxycarbonyl-2-piperazinone (21.92 g) and 1-(4-pyridyl)-4-piperidone (15.51 g) in ethanol (500 ml) was dehydrated using a Soxlet extractor packed with molecular sieves 4A while refluxing for 24 hours. The reaction mixture was concentrated to obtain a residue, which was dissolved in methanol (300 ml) and combined with acetic acid (18.26 g) with cooling on ice followed by sodium cycanoborohydride (7.16 g) and then stirred at 0° C. for 3 hours. The reaction mixture was concentrated, and the residue was combined with a 1N aqueous solution of sodium hydroxide, and extracted with methylene chloride. The extract was washed with water and brine, dried and concentrated to obtain 4-benzyloxycarbonyl-1-[1-(4-pyridyl)-4-piperidinylamino]-2-piperazinone (25.29 g) as a pale yellow amorphous material.

後処理

  1. temperaturewhile refluxing for 24 hours
  2. concentrationThe reaction mixture was concentrated
  3. customto obtain a residue, which
  4. temperaturewith cooling on ice
  5. concentrationThe reaction mixture was concentrated
  6. extractionextracted with methylene chloride
  7. washThe extract was washed with water and brine
  8. customdried
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-75179fc5facb4f8ea50aa3e0bad61c1a
出典データセット
uspto-grants-2004_04
特許番号
US06723722B1

反応ノート

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