CBz-D-phenylglycine 4-(1-methylpiperidin-4-yl)piperidinamide → D-Phenylglycine 4-(1-methylpiperidin-4-yl)piperidinamide

HRID 2229586Notes

Reaction equation

HRID 2229586 reaction equation
C1C=CC(COC([NH:11][C@@H:12]([C:19]([OH:21])=[O:20])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=O)=CC=1.[CH3:22][N:23]1[CH2:28][CH2:27][CH:26]([CH:29]2[CH2:34][CH2:33][N:32]([C:35]([NH2:37])=[O:36])[CH2:31][CH2:30]2)[CH2:25][CH2:24]1.[H][H]>CO.[Pd]>[CH:16]1[CH:15]=[CH:14][C:13]([C@@H:12]([NH2:11])[C:19]([OH:21])=[O:20])=[CH:18][CH:17]=1.[CH3:22][N:23]1[CH2:24][CH2:25][CH:26]([CH:29]2[CH2:34][CH2:33][N:32]([C:35]([NH2:37])=[O:36])[CH2:31][CH2:30]2)[CH2:27][CH2:28]1

Participants

5

Reactant 2

HCID 131722772CBz-D-phenylglycine 4-(1-methylpiperidin-4-yl)piperidinamideHCID 178418361HCID 178418361, compound

Product 1

HCID 131722773D-Phenylglycine 4-(1-methylpiperidin-4-yl)piperidinamideYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A vigorously stirred solution of CBz-D-phenylglycine-4-(1-methylpiperidin-4-yl)piperidinamide (1.1 g, 2.45 mmol) in methanol (120 ml), containing Palladium on carbon (200 mg) was treated with hydrogen gas (balloon) at atmospheric pressure overnight. The reaction mixture was filtered through celite and concentrated to yield the title compound as a colourless oil (585 mg, 76%).

Workup

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-b9477f48cf734c3b8f1694658a73b8c0
Source dataset
uspto-grants-2002_07
Patent number
US06420438B1

Reaction notes

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