Benzoyl chloride → n-(1-Benzoylpiperidin-4-yl)-n'-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}urea

HRID 1371453ノート

反応式

HRID 1371453 の反応式
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[Cl:11][C:12]1[CH:13]=[C:14]([CH:33]=[CH:34][C:35]=1[Cl:36])[CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH:18]([CH2:22][NH:23][C:24]([NH:26][CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[O:25])[CH2:17]1.C(N(CC)C(C)C)(C)C>ClCCl>[C:1]([N:30]1[CH2:31][CH2:32][CH:27]([NH:26][C:24]([NH:23][CH2:22][CH:18]2[O:19][CH2:20][CH2:21][N:16]([CH2:15][C:14]3[CH:33]=[CH:34][C:35]([Cl:36])=[C:12]([Cl:11])[CH:13]=3)[CH2:17]2)=[O:25])[CH2:28][CH2:29]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 17984664HCID 17984664、化合物

生成物 1

HCID 17984690n-(1-Benzoylpiperidin-4-yl)-n'-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}urea

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
23 °C

実験手順

Benzoyl choride (0.014 ml) was added to a solution of Intermediate 16 (0.04 g) and N,N-diisopropylethylamine (0.048 ml) in dichloromethane (3 ml). The solution was stirred for 5 h at 23° C. The solvent was removed in vacuo and the residue purified by solid phase extraction (Isolute SCX sulphonic acid column) eluting with methanol followed by 10% 0.880 ammonia solution in methanol. The basic fraction was concentrated in vacuo and the residue was further purified using a silica gel solid phase extraction cartridge (1 g Varian Bond Elut), eluting sequentially with dichloromethane, ethyl acetate, acetone, acetonitrile, and methanol, to give the title compound as a clear gum (0.024 g).

後処理

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by solid phase extraction (Isolute SCX sulphonic acid column)
  3. washeluting with methanol
  4. concentrationThe basic fraction was concentrated in vacuo
  5. customthe residue was further purified
  6. extractiona silica gel solid phase extraction cartridge (1 g Varian Bond Elut)
  7. washeluting sequentially with dichloromethane, ethyl acetate, acetone, acetonitrile, and methanol

出典と根拠

ORDレコード
ord-ea26f59dc24c48f59bbc5afc970af945
出典データセット
uspto-grants-2007_01
特許番号
US07157457B2

反応ノート

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