Sodium Hydroxide → Vamicamide

HRID 1590086Notes

Reaction equation

HRID 1590086 reaction equation
Cl.[CH3:2][N:3]([CH3:23])[C@H:4]([CH3:22])[CH2:5][C@@:6]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[C:7]([NH2:9])=[O:8].[OH-].[Na+]>O>[CH3:23][N:3]([CH3:2])[C@H:4]([CH3:22])[CH2:5][C@@:6]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[C:7]([NH2:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69111440HCID 69111440, compound

Product 1

HCID 65967VamicamideYield 90.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of (±)-(2R*,4R*)-4-dimethylamino-2-phenyl-2-(2-pyridyl)valeramide hydrochloride (20 g) in water (80 ml) were added seed crystals (0.02 g) and a solution of sodium hydroxide (2.47 g) in water (80 ml) was dropwise added thereto at 20-25° C. over a period of 30 minutes. The mixture was stirred at the same temperature for 1 hour. The resulting crystals were recovered by filtration, washed with water and dried to give (±)-(2R*,4R*)-4-dimethylamino-2-phenyl-2-(2-pyridyl)-valeramide (16.1 g).

Workup

  1. filtrationThe resulting crystals were recovered by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-684e18c4ccc24c08b22ba25fdc1b3405
Source dataset
uspto-grants-1993_04
Patent number
US05202331

Reaction notes

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