Methanol → HCID 11236182, compound

HRID 1765993Notes

Reaction equation

HRID 1765993 reaction equation
CO.C([N:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:31])[C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=2)[C@H:12]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[C:35]([OH:40])[CH:34]=2)[CH2:11]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].O>[F:30][C:27]([F:28])([F:29])[C:19]1[CH:18]=[C:17]([CH:22]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:20]=1)[C:16]([N:13]1[CH2:14][CH2:15][NH:10][CH2:11][C@H:12]1[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([CH3:39])=[C:35]([OH:40])[CH:34]=1)=[O:31]

Participants

6

Reactant 3

HCID 887MethanolHCID 2723923Ammonium formateHCID 11226424HCID 11226424, compound

Product 1

HCID 11236182HCID 11236182, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Into a mixed solution of methanol (270 l) and water (30 l) were charged (2R)-4-benzyl-1-[3,5-bis(trifluoromethyl)-benzoyl]-2-(3-hydroxy-4-methylbenzyl)piperazine (30.0 kg), ammonium formate (8.8 kg) and 10% palladium on carbon (wet condition: 50%, 1.5 kg). They were allowed to react at an inside temperature of 50 to 55° C. for 4 hours. After the reaction was completed, the reaction solution was cooled to room temperature, clarified and filtered, and washed with methanol (90 l). Water (480 l) was added dropwise to the combined filtrate and washings at room temperature and crystallization was effected under ice-cooling for 8 hours. Crystals were collected by filtration, washed with water (90 l) and dried under reduced pressure to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3-hydroxy-4-methylbenzyl)-piperazine (23.7 kg, yield 94.8%) in the form of white crystals.

Workup

  1. customto react at an inside temperature of 50 to 55° C. for 4 hours
  2. filtrationfiltered
  3. washwashed with methanol (90 l)
  4. additionWater (480 l) was added dropwise to the combined filtrate and washings at room temperature
  5. customcrystallization
  6. temperaturecooling for 8 hours
  7. filtrationCrystals were collected by filtration
  8. washwashed with water (90 l)
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-fbff6921c9cc469cbf6d81df2738743a
Source dataset
uspto-grants-2007_06
Patent number
US07229992B2

Reaction notes

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