HCID 18452746, compound → HCID 18519838, compound

HRID 230113Notes

Reaction equation

HRID 230113 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10](=[O:33])[CH2:11][N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([OH:32])[CH2:20][NH:21]C(OCC2C=CC=CC=2)=O)[CH2:14][CH2:13]1>CO>[NH2:21][CH2:20][CH:19]([OH:32])[CH2:18][N:15]1[CH2:16][CH2:17][N:12]([CH2:11][C:10]([NH:9][C:3]2[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])=[O:33])[CH2:13][CH2:14]1

Participants

3

Reactant 1

HCID 18452746HCID 18452746, compound

Product 1

HCID 18519838HCID 18519838, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(2,6-dimethylphenyl)-2-(4-{2-hydroxy-3-[(phenylmethoxy)-carbonylamino]propyl}piperazinyl)acetamide in methanol (70 mL) at room temperature was added under a steady flow of nitrogen Pd/C (10% w/w, 0.337 g). Hydrogen gas was bubbled through the reaction mixture via a septum with a needle as outlet for 2 minutes, and the reaction was stirred under a positive hydrogen pressure for two hours. Nitrogen was blown over the suspension before it was filtered over celite. The filtrate was evaporated to give 2-[4-(3-amino-2-hydroxypropyl)piperazin-1-yl]-N-(2,6-dimethylphenyl)acetamide, a compound of formula (6), as a clear oil (2.0 g).

Workup

  1. customHydrogen gas was bubbled through the reaction mixture via a septum with a needle as outlet for 2 minutes
  2. filtrationwas filtered over celite
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-026639a5c6934f60ab6127304b0b0d49
Source dataset
uspto-grants-2009_07
Patent number
US07566717B2

Reaction notes

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