Dimethylformamide → 4-[(1-benzylpiperidin-3-yl)methyl]-N-(3,4-dichlorophenyl)-3-oxopiperazine-1-carboxamide

HRID 603178Notes

Reaction equation

HRID 603178 reaction equation
Cl.Cl.[CH2:3]([N:10]1[CH2:15][CH2:14][CH2:13][CH:12]([CH2:16][N:17]2[CH2:22][CH2:21][NH:20][CH2:19][C:18]2=[O:23])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)C(C)C)(C)C.CN(C)C=O.[Cl:38][C:39]1[CH:40]=[C:41]([N:46]=[C:47]=[O:48])[CH:42]=[CH:43][C:44]=1[Cl:45]>ClCCl>[CH2:3]([N:10]1[CH2:15][CH2:14][CH2:13][CH:12]([CH2:16][N:17]2[CH2:22][CH2:21][N:20]([C:47]([NH:46][C:41]3[CH:42]=[CH:43][C:44]([Cl:45])=[C:39]([Cl:38])[CH:40]=3)=[O:48])[CH2:19][C:18]2=[O:23])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 76073,4-Dichlorophenyl isocyanateHCID 81531DiisopropylethylamineHCID 672206771-[(1-Benzylpiperidin-3-yl)methyl]piperazin-2-one dihydrochloride

Product 1

HCID 116772464-[(1-benzylpiperidin-3-yl)methyl]-N-(3,4-dichlorophenyl)-3-oxopiperazine-1-carboxamideYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-[(1-benzylpiperidin-3-yl)methyl]piperazin-2-one dihydrochloride (83 mg) in dichloromethane (10 mL) was added N,N-di-iso-propylethylamine (0.1 mL). After 1 minute dimethylformamide (1 mL) was added followed by 3,4-dichlorophenyl isocyanate (47 mg). The solution was stirred for 5 minutes and then partitioned between dichloromethane and water. The organic layer was separated, dried over sodium sulfate and evaporated. The residue was purified by silica column chromatography, eluting with a gradient of 0 to 10% MeOH in dichloromethane to give the title compound as a white solid (92 mg, 84%).

Workup

  1. custompartitioned between dichloromethane and water
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was purified by silica column chromatography
  6. washeluting with a gradient of 0 to 10% MeOH in dichloromethane

Sources & evidence

ORD record
ord-f8ecd4a1d06646f886e016f723e50dec
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

Loading…