4-Methylmorpholine → 1,1-Dimethylethyl 4-[[2-(4-chlorophenyl)acetyl]amino]-1-piperidinecarboxylate

HRID 457169ノート

反応式

HRID 457169 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](O)=[O:24])=[CH:18][CH:17]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:23](=[O:24])[CH2:22][C:19]2[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 5

HCID 79724-MethylmorpholineHCID 15880(4-Chlorophenyl)acetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 12682914-Amino-1-Boc-piperidine

生成物 1

HCID 470691701,1-Dimethylethyl 4-[[2-(4-chlorophenyl)acetyl]amino]-1-piperidinecarboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-amino-piperidine 1-carboxylic acid tert-butyl ester (0.44 g, 2.2 mmol) and 4-chlorophenyl acetic acid (0.34 g, 2 mmol) in dichloromethane (10 mL) were added EDCI (0.55 g, 2.8 mmol), HOBT (0.42 g, 2.8 mmol) and N-methylmorpholine (0.6 g, 6 mmol) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo, diluted with dichloromethane and extracted with saturated aqueous sodium bicarbonate solution. The aqueous layer was back extracted twice with dichloromethane. The combined organics were dried over sodium sulfate and concentrated in vacuo. Crude product was purified using a short plug of silica gel using ethyl acetate to give the desired product

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with dichloromethane
  3. extractionextracted with saturated aqueous sodium bicarbonate solution
  4. extractionThe aqueous layer was back extracted twice with dichloromethane
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customCrude product was purified

出典と根拠

ORDレコード
ord-a90de48143ea4bb9be0fe9de54eefdc5
出典データセット
uspto-grants-2007_03
特許番号
US07186729B2

反応ノート

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