1,1'-Carbonyldiimidazole → HCID 69970027, compound

HRID 343467Notes

Reaction equation

HRID 343467 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][C@@H:13]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)[CH2:14][N:15]([CH3:24])[C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:7][CH2:6]1.[C:33](N1C=CN=C1)(N1C=CN=C1)=[O:34]>C(Cl)(Cl)Cl.ClCCl>[ClH:31].[Cl:32][C:27]1[CH:26]=[C:25]([C@H:13]([CH2:12][CH2:11][N:8]2[CH2:9][CH2:10][CH:5]([N:4]3[CH2:3][CH2:2][NH:1][C:33]3=[O:34])[CH2:6][CH2:7]2)[CH2:14][N:15]([CH3:24])[C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:30]=[CH:29][C:28]=1[Cl:31]

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 54469677HCID 54469677, compound

Product 1

HCID 69970027HCID 69970027, compoundYield 121.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of (S)-N-[4-[4-(2-aminoethylamino)-piperidino]-2-(3,4-dichlorophenyl)butyl]-N-methylbenzamide (0.356 g) and 1,1'-carbonyldiimidazole (0.157 g) in chloroform (6 mL) was heated at reflux for 2 hours. The reaction mixture was diluted with dichloromethane, washed (aqueous sodium bicarbonate), dried, evaporated, and chromatographed, with dichloromethane:methanol (gradient 98:2, 90:10) as eluent. The resulting material was dissolved in dichloromethane, precipitated as the hydrochloride salt with ethereal hydrogen chloride, evaporated, and placed under high vacuum overnight to give the title compound as a white solid (0.244 g); MS: m/z=503(M+1); Analysis for C26H32Cl2N4O2.1.70 HCl.0.20 (C2H5)2O: Calculated: C, 55.47; H, 6.20; N, 9.65; Found: C, 55.47; H, 6.35; N, 9.44.

Workup

  1. temperatureat reflux for 2 hours
  2. washwashed (aqueous sodium bicarbonate)
  3. customdried
  4. customevaporated
  5. customchromatographed, with dichloromethane
  6. dissolutionThe resulting material was dissolved in dichloromethane
  7. customprecipitated as the hydrochloride salt with ethereal hydrogen chloride
  8. customevaporated
  9. customplaced under high vacuum overnight

Sources & evidence

ORD record
ord-0ccd03c7b123414dafc6a8a92932abae
Source dataset
uspto-grants-1999_01
Patent number
US05861392

Reaction notes

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