Water → HCID 70148863, compound

HRID 1278604Notes

Reaction equation

HRID 1278604 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][CH2:8][C:9]1([CH2:15][N:16]2[CH2:21][CH2:20][N:19]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:18][CH2:17]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[H-].[K+].[CH2:32](I)[CH3:33].O>CN(C)C=O>[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:8][C:9]1([CH2:15][N:16]2[CH2:17][CH2:18][N:19]([CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:20][CH2:21]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)[CH2:32][CH3:33])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 82127Potassium hydrideHCID 18430867HCID 18430867, compound

Product 1

HCID 70148863HCID 70148863, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl[1-[(4-benzyl-1-piperazinyl)methyl]cyclohexyl]methylcarbamate (770 mg/1.92 mmol) in dimethylformamide (10 ml) was added potassium hydride (157 mg/3.84 mmol) at 0° C. and the resulting solution was stirred for 30 minutes at the same temperature. Ethyliodide (0.46 ml/5.76 mmol) was added to the solution and the resulting mixture was stirred for 6 hours at ambient temperature Water (20 ml) was added for quenching and the mixture was extracted with ethyl acetate (100 ml). The extract was washed with brine (20 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (Si/230-400 mesh/20 g/dichloromethane:methanol=100:0-100:2-100:4-100:6) to give a colorless oil (730 mg/89%).

Workup

  1. additionwas added
  2. customfor quenching
  3. extractionthe mixture was extracted with ethyl acetate (100 ml)
  4. washThe extract was washed with brine (20 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (Si/230-400 mesh/20 g/dichloromethane:methanol=100:0-100:2-100:4-100:6)
  9. customto give a colorless oil (730 mg/89%)

Sources & evidence

ORD record
ord-a610f42ac8b4461595965b2836e87438
Source dataset
uspto-grants-2002_09
Patent number
US06444677B2

Reaction notes

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