Acetic Acid → 1,1-Dimethylethyl 4-[[4-(4-chlorophenoxy)phenyl]amino]-1-piperidinecarboxylate

HRID 630322

반응식

HRID 630322 반응식
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[Cl:15][C:16]1[CH:29]=[CH:28][C:19]([O:20][C:21]2[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=2)=[CH:18][CH:17]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[Cl:15][C:16]1[CH:29]=[CH:28][C:19]([O:20][C:21]2[CH:27]=[CH:26][C:24]([NH:25][CH:2]3[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]3)=[CH:23][CH:22]=2)=[CH:18][CH:17]=1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 75784-(4-Chlorophenoxy)anilineHCID 516892Sodium BicarbonateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 684895971,1-Dimethylethyl 4-[[4-(4-chlorophenoxy)phenyl]amino]-1-piperidinecarboxylate수율 71.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In a similar manner as described above in Paragraph A, a solution of 1,1-dimethylethyl 4-oxo-1-piperidinecarboxylate (1 g, 4.5 mmol) and 4-(4-chlorophenoxy)aniline (1 g, 5 mmol) in dichloromethane was stirred as acetic acid (0.39 g, 6.5 mmol) was added. After 15 minutes, sodium triacetoxyborohydride (2 g, 9.4 mmol) was added and the reaction was stirred for 3 days. The reaction was treated with aqueous sodium bicarbonate. The organic layer was washed with water, dried, and concentrated. Purification by flash chromatography on silica gel using a gradient of ethyl acetate in hexane gave 1.3 g of 1,1-dimethylethyl 4-[[4-(4-chlorophenoxy)phenyl]amino]-1-piperidinecarboxylate.

후처리

  1. additionwas added
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-1a8a787073444734bf65dbe819451a08
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315509B2

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