Piperidine → Biphenyl-2-ylcarbamic acid 1-{2-[(3-aminopropyl)methylcarbamoyl]ethyl}piperidin-4-yl ester

HRID 1039826노트

반응식

HRID 1039826 반응식
C1C2C(COC([NH:18][CH2:19][CH2:20][CH2:21][N:22]([CH3:49])[C:23]([CH2:25][CH2:26][N:27]3[CH2:32][CH2:31][CH:30]([O:33][C:34](=[O:48])[NH:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[CH2:29][CH2:28]3)=[O:24])=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>C(Cl)Cl>[NH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH3:49])[C:23]([CH2:25][CH2:26][N:27]1[CH2:28][CH2:29][CH:30]([O:33][C:34](=[O:48])[NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH2:31][CH2:32]1)=[O:24]

참가 물질

4

반응물 2

HCID 8082PiperidineHCID 66770111Biphenyl-2-ylcarbamic Acid 1-(2-{[3-(9H-Fluoren-9-ylmethoxycarbonylamino)propyl]methylcarbamoyl}ethyl)piperidin-4-yl Ester

생성물 1

HCID 66770333Biphenyl-2-ylcarbamic acid 1-{2-[(3-aminopropyl)methylcarbamoyl]ethyl}piperidin-4-yl ester수율 69.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To biphenyl-2-ylcarbamic acid 1-(2-{[3-(9H-fluoren-9-ylmethoxycarbonyl-amino)propyl]methylcarbamoyl}ethyl)piperidin-4-yl ester (2.2 g, 3.3 mmol) was added a 10% solution of piperidine (0.31 g, 3.3 mmol) in DCM (3.2 mL) and the resulting mixture was shaken at room temperature for 1 h. The mixture was concentrated under reduced pressure and the residue was dissolved in DCM (100 mL). This mixture was washed with water (2×20 mL) and then extracted with ammonium chloride (1 N, 2×20 mL). The layers were separated and DCM was added to the aqueous layer. The aqueous layer was made basic by addition of aqueous potassium hydroxide (1 N) and the layers were separated. The organic layer was washed with aqueous potassium hydroxide (1 N, 2×20 mL) and brine (1×20 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (1.0 g, 66% yield) as a clear oil.

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in DCM (100 mL)
  3. washThis mixture was washed with water (2×20 mL)
  4. extractionextracted with ammonium chloride (1 N, 2×20 mL)
  5. customThe layers were separated
  6. additionDCM was added to the aqueous layer
  7. additionThe aqueous layer was made basic by addition of aqueous potassium hydroxide (1 N)
  8. customthe layers were separated
  9. washThe organic layer was washed with aqueous potassium hydroxide (1 N, 2×20 mL) and brine (1×20 mL)
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c1e69d4ab3e84b4bba37e49d60dbfb5a
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551978B2

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