Ethanol → 1-(2-(Methylamino)ethyl)piperidin-4-yl [1,1'-biphenyl]-2-ylcarbamate

HRID 388635

Reaction equation

HRID 388635 reaction equation
C([CH2:8][NH:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([O:18][C:19](=[O:33])[NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:14][CH2:13]1)C1C=CC=CC=1.CCO.C(OC(C)C)(=O)C>C(Cl)Cl>[CH3:8][NH:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([O:18][C:19](=[O:33])[NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 702EthanolHCID 7915Isopropyl AcetateHCID 57436142Biphenyl-2-ylcarbamic acid 1-[2-(benzylmethylamino)ethyl]piperidin-4-yl ester

Product 1

HCID 566436031-(2-(Methylamino)ethyl)piperidin-4-yl [1,1'-biphenyl]-2-ylcarbamateYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a Parr hydrogenation flask was added biphenyl-2-ylcarbamic acid 1-[2-(benzylmethylamino)ethyl]piperidin-4-yl ester (40 g, 0.09 mol; prepared as described in Preparation 5) and EtOH (0.5 L). The flask was flushed with nitrogen gas and palladium on activated carbon (15 g, 10 wt % dry basis, 37% wt/wt) was added along with HOAc (20 mL). The mixture was kept on the Parr hydrogenator under a hydrogen atmosphere (˜50 psi) for 3 hours. The mixture was then filtered and washed with EtOH. The filtrate was condensed and the residue was dissolved in a minimal amount of DCM. Isopropyl acetate (10 volumes) was added slowly to form a solid which was collected to provide 22.0 g of the title compound (70% yield). MS m/z: [M+H+] calcd for C21H27N3O2, 354.2. found, 354.3. Rf=2.96 min (10-70 ACN:H2O, reverse phase HPLC).

Workup

  1. customThe flask was flushed with nitrogen gas and palladium on activated carbon (15 g, 10 wt % dry basis, 37% wt/wt)
  2. additionwas added along with HOAc (20 mL)
  3. customfor 3 hours
  4. filtrationThe mixture was then filtered
  5. washwashed with EtOH
  6. customcondensed
  7. customto form a solid which
  8. customwas collected

Sources & evidence

ORD record
ord-6cf1a92d8bfc4f698cdc28ad56cb67fc
Source dataset
uspto-grants-2013_02
Patent number
US08377966B2

Linked notes

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