Hydrochloric Acid → HCID 57236009, compound

HRID 896403Notes

Reaction equation

HRID 896403 reaction equation
[OH:1]O.[CH2:3]([N:6]1[C@H:11]([CH3:12])[CH2:10][N:9]([C@H:13]([C:21]2[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=2)[C:24]#[N:25])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)[C@@H:8]([CH3:29])[CH2:7]1)[CH:4]=[CH2:5].[OH-].[Na+].Cl>C(O)C>[CH2:3]([N:6]1[C@H:11]([CH3:12])[CH2:10][N:9]([C@H:13]([C:21]2[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=2)[C:24]([NH2:25])=[O:1])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)[C@@H:8]([CH3:29])[CH2:7]1)[CH:4]=[CH2:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 11783384HCID 11783384, compound

Product 1

HCID 57236009HCID 57236009, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Hydrogen peroxide (0.5 mL of a 30% by weight solution) was added to a mixture of the benzonitrile (0.50 g, 1.4 mmol), 0.7 mL of 10N aqueous sodium hydroxide and 3 mL of ethanol. The reaction was exothermic with gas evolution and formation of a white precipitate. After a few minutes, the mixture was carefully heated under a reflux condenser in an oil bath at 60° C. for three hours. After cooling to room temperature, 6N aqueous hydrochloric acid was added to adjust the pH to 8. The mixture was evaporated to dryness under vacuum, and the residue was extracted between ethyl acetate and pH 8 buffer solution. The organic layer was washed with pH 8 buffer and brine, dried over sodium sulfate, and the solvent was evaporated to give 0.42 g (79%) of (±)-3-((αR*)-α-((2S*,5R*)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)benzamide as a bright yellow solid.

Workup

  1. waitAfter a few minutes
  2. temperatureAfter cooling to room temperature
  3. customThe mixture was evaporated to dryness under vacuum
  4. extractionthe residue was extracted between ethyl acetate and pH 8 buffer solution
  5. washThe organic layer was washed with pH 8 buffer
  6. dry with materialbrine, dried over sodium sulfate
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-916bf4d6637d4151a7c1be89120c2602
Source dataset
uspto-grants-2005_07
Patent number
US06919350B2

Reaction notes

Loading…