Water → HCID 18430853, compound

HRID 1278621Notes

Reaction equation

HRID 1278621 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2([CH2:21][NH:22][C:23](=[O:28])[CH2:24][CH2:25][CH2:26]Cl)[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].O>CN(C)C=O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2([CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][C:23]3=[O:28])[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 18430928HCID 18430928, compound

Product 1

HCID 18430853HCID 18430853, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of N-[[1-[2-(4-benzyl-1-piperazinyl)ethyl]cyclopentyl]methyl]-4-chlorobutanamide (664 mg) in dimethylformamide(5.5 ml) was added sodium hydride(60% in oil, 98 mg) at room temperature and the mixture was stirred at 70° C. for 5 hours. After cooling down, water (3 ml) was added and the organic layers were extracted with ethyl acetate (15 ml). The extract was washed with brine (4 ml), dried over magnesium sulfate filtered and concentrated in vacuo. The residue was purified by column chromatography (NH2 gel, 230-400 mesh/20 g/hexane:ethyl acetate=2:1-1:2) to give a yellow oil (408 mg/67%).

Workup

  1. temperatureAfter cooling down
  2. extractionthe organic layers were extracted with ethyl acetate (15 ml)
  3. washThe extract was washed with brine (4 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (NH2 gel, 230-400 mesh/20 g/hexane:ethyl acetate=2:1-1:2)
  8. customto give a yellow oil (408 mg/67%)

Sources & evidence

ORD record
ord-3fde1b04155649fa9a0b0befaf4fce83
Source dataset
uspto-grants-2002_09
Patent number
US06444677B2

Reaction notes

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