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

HRID 1097036Notes

Reaction equation

HRID 1097036 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-962f088e957948308b9cc01da1629952
Source dataset
uspto-grants-2012_03
Patent number
US08138345B2

Reaction notes

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