Water → HCID 53871969, compound

HRID 1374988Notes

Reaction equation

HRID 1374988 reaction equation
[H-].[Na+].[CH2:3]([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)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:41][O:42][CH2:43][CH2:44][O:45][CH2:46]Cl.O>CN(C)C=O>[CH2:3]([N:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:31])[C:17]2[CH:22]=[C:21]([C:23]([F:24])([F:25])[F:26])[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]([O:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH3:46])[CH:34]=2)[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 11226424HCID 11226424, compound

Product 1

HCID 53871969HCID 53871969, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil, 18 mg) was added by small portions to an ice-cooled solution of (2R)-4-benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3-hydroxy-4-methylbenzyl)piperazine (0.20 g) in N,N-dimethylformamide (2 ml) below 5° C. under nitrogen atmosphere. After the mixture was stirred for 5 minutes, (2-methoxyethoxy)methyl chloride (0.064 ml) was added to the mixture. The whole was stirred at room temperature for 2.5 hours, and thereto water was added. The whole was extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using mixed solvents of hexane and ethyl acetate (7:3). The fractions containing the objective compound were collected and evaporated under reduced pressure to give (2R)-4-benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]-2-[3-[(2-methoxyethoxy)methoxy]-4-methylbenzyl]piperazine (0.21 g) as an oil.

Workup

  1. stirringThe whole was stirred at room temperature for 2.5 hours
  2. extractionThe whole was extracted with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel using
  6. additionmixed solvents of hexane and ethyl acetate (7:3)
  7. additionThe fractions containing the objective compound
  8. customwere collected
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2adb3d39ca864aaa8d7cd8f566d78f0e
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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