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

HRID 1384892Notes

Reaction equation

HRID 1384892 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-2e601390331741ff9e9e8717f24d47ad
Source dataset
uspto-grants-2001_07
Patent number
US06262069B1

Reaction notes

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