Water → [1-(2-Amino-5-phenylcarbamoyl-phenyl)-piperidin-4-ylmethyl]-carbamic acid tert-butyl ester

HRID 1773577노트

반응식

HRID 1773577 반응식
[C:1]([O:5][C:6](=[O:33])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[C:19]([C:21](=[O:29])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:18]=[CH:17][C:16]=2[N+:30]([O-])=O)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C.O.[Cl-].[NH4+]>C(O)C.[Fe]>[C:1]([O:5][C:6](=[O:33])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[C:19]([C:21](=[O:29])[NH:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:18]=[CH:17][C:16]=2[NH2:30])[CH2:11][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 66664552[1-(2-Nitro-5-phenylcarbamoyl-phenyl)-piperidin-4-ylmethyl]-carbamic acid tert-butyl ester

생성물 1

HCID 66664613[1-(2-Amino-5-phenylcarbamoyl-phenyl)-piperidin-4-ylmethyl]-carbamic acid tert-butyl ester수율 98.8%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

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온도
80 °C

실험 절차

To a solution of [1-(2-nitro-5-phenylcarbamoyl-phenyl)-piperidin-4-ylmethyl]-carbamic acid tert-butyl ester (0.13 g, 0.286 mmol) in a mixture of ethanol (8 mL), ethyl acetate (3 mL) and water (3 mL) were added ammonium chloride (0.12 g, 7.6 mmol) and iron powder (0.12 g, 7.5 mmol) and the resulting mixture was heated at 80° C. for 4 hours. The reaction mixture was filtered through a CELITE™ pad, the filter cake was washed with ethyl acetate. The filtrate was washed with and aqueous solution of sodium bicarbonate (5%) and with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to afford 0.12 g (quantitative yield) of [1-(2-amino-5-phenylcarbamoyl-phenyl)-piperidin-4-ylmethyl]-carbamic acid tert-butyl ester as light yellow foam.

후처리

  1. filtrationThe reaction mixture was filtered through a CELITE™ pad
  2. washthe filter cake was washed with ethyl acetate
  3. washThe filtrate was washed with and aqueous solution of sodium bicarbonate (5%)
  4. dry with materialwith brine, dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-3bd1241678184f7ba5453fea04b83d3d
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255110B2

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