HCID 53871969, compound → HCID 53740990, compound

HRID 1374989Notes

Reaction equation

HRID 1374989 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:29])[C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=2)[C@H:10]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[C:33]([O:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH3:44])[CH:32]=2)[CH2:9]1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-].[C]>[F:28][C:25]([F:26])([F:27])[C:17]1[CH:16]=[C:15]([CH:20]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:18]=1)[C:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][C@H:10]1[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[C:33]([O:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH3:44])[CH:32]=1)=[O:29]

Participants

4

Reactant 1

HCID 53871969HCID 53871969, compound

Product 1

HCID 53740990HCID 53740990, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of (2R)-4-benzyl-1-[3,5-bis(trifluoromethyl)-benzoyl]-2-[3-[(2-methoxyethoxy)methoxy]-4-methylbenzyl]-piperazine (0.38 g) in methanol (6 ml) was hydrogenated over 20% palladium hydroxide-carbon (0.06 g) at room temperature under atmospheric pressure for 8 hours. After removal of the catalyst by filtration through Celite®, the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using mixed solvents of dichloromethane and methanol (30:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-[3-[(2-methoxyethoxy)methoxy]-4-methylbenzyl]piperazine (0.32 g) as an oil.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration through Celite®
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel using
  5. additionmixed solvents of dichloromethane and methanol (30:1)
  6. additionThe fractions containing the objective compound
  7. customwere collected
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-89e7a7b299ff45fe8d6f2fb92951f47e
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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