4-Amino-3-chlorobenzoic acid → 4-amino-3-chloro-N-(1-methyl-4-piperidyl)benzamide

HRID 1676530ノート

反応式

HRID 1676530 の反応式
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[Cl:11].[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1.C(N(C(C)C)C(C)C)C>CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+]>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:12][CH:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[O:8])=[CH:4][C:3]=1[Cl:11]

参加物

6

反応物 3

HCID 172114-Amino-3-chlorobenzoic acidHCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidine

生成物 1

HCID 580150334-amino-3-chloro-N-(1-methyl-4-piperidyl)benzamide収率 0.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 10340Sodium Carbonate溶媒

実験手順

To a solution of 1.0 g (5.9 mole) of 4-amino-3-chlorobenzoic acid, 0.8 g (7.0 mole) of 4-amino-1-methyl-piperidine and 4.14 mL (23 mmole) of ethyldiisopropyl amine in 20 mL of dimethylformamide was added a solution of 2.4 g (6.4 mole) of 1-(di-1-pyrrolidinylmethylene)-1H-benzotriazolium 3-oxide hexafluorophosphate in 5 mL of dimethylformamide. The mixture was stirred at room temperature for 2 hours, then diluted with ice water and saturated sodium carbonate. The mixture was extracted with ethyl acetate twice. The combined organic layers were washed three times with sodium carbonate, three times with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel chromatography, eluting with dichloromethane-methanol (gradient, 100:0-60:40) gave 1.41 g of 4-amino-3-chloro-N-(1-methyl-piperidin-4-yl)-benzamide as a solid.

後処理

  1. extractionThe mixture was extracted with ethyl acetate twice
  2. washThe combined organic layers were washed three times with sodium carbonate, three times with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel chromatography
  7. washeluting with dichloromethane-methanol (gradient, 100:0-60:40)

出典と根拠

ORDレコード
ord-b7512b0f5104436c920a7cd4d112d07f
出典データセット
uspto-grants-2011_08
特許番号
US08003785B2

反応ノート

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