1,1'-Carbonyldiimidazole → HCID 15645953, compound

HRID 1196872Notes

Reaction equation

HRID 1196872 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:13][C:14]1[CH:15]=[C:16]([CH2:21][C:22]([OH:24])=O)[CH:17]=[CH:18][C:19]=1[Cl:20].[C:25]1([CH2:31][N:32]2[CH2:37][CH2:36][NH:35][CH:34]([CH2:38][OH:39])[CH2:33]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl>[Cl:13][C:14]1[CH:15]=[C:16]([CH2:21][C:22]([N:35]2[CH2:36][CH2:37][N:32]([CH2:31][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:33][CH:34]2[CH2:38][OH:39])=[O:24])[CH:17]=[CH:18][C:19]=1[Cl:20]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 798743,4-Dichlorophenylacetic acidHCID 2756656(4-benzylpiperazin-2-yl)methanol

Product 1

HCID 15645953HCID 15645953, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

1,1'-Carbonyldiimidazole (236 mg) was added to a stirred solution of 3,4-dichlorophenylacetic acid (314 mg) in dry dichloromethane (6 ml) at room temperature under nitrogen. The resulting solution was stirred at room temperature for 1 h and added dropwise to a cooled solution of 4-(phenylmethyl)-2-piperazinemethanol (300 mg) in dry dichloromethane (3 ml) and stirred at room temperature for 19 h. The reaction mixture was diluted with dichloromethane (5 ml) and washed with 2N sodium carbonate solution (3×10 ml). The organic layer was dried and evaporated to give an oil which was purified by flash column chromatography using gradient elution with dichloromethane:ethyl acetate (2:1), dichloromethane:ethyl acetate (1:1) and dichloromethane:methanol (9:1) to give the title compound as a solid (200 mg). m.p. 148°-150°.

Workup

  1. stirringstirred at room temperature for 19 h
  2. washwashed with 2N sodium carbonate solution (3×10 ml)
  3. customThe organic layer was dried
  4. customevaporated
  5. customto give an oil which
  6. customwas purified by flash column chromatography
  7. washelution with dichloromethane:ethyl acetate (2:1), dichloromethane:ethyl acetate (1:1) and dichloromethane:methanol (9:1)

Sources & evidence

ORD record
ord-ba0a155278bc4524b6d049331b8871ed
Source dataset
uspto-grants-1992_05
Patent number
US05116842

Reaction notes

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