Ethyl chloroformate → HCID 22745278, compound

HRID 47536Notes

Reaction equation

HRID 47536 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH2:12][CH2:11][CH:10]([N:13]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[NH:15][C:14]3=[O:22])[CH2:9][CH2:8]2)[CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.Cl[C:33]([O:35][CH2:36][CH3:37])=[O:34].C(=O)(O)[O-].[Na+]>ClCCl.C(Cl)(Cl)Cl>[CH2:36]([O:35][C:33]([N:1]1[CH2:2][CH2:3][CH:4]([N:7]2[CH2:8][CH2:9][CH:10]([N:13]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[NH:15][C:14]3=[O:22])[CH2:11][CH2:12]2)[CH2:5][CH2:6]1)=[O:34])[CH3:37]

Participants

7

Reactant 4

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 15839552HCID 15839552, compound

Product 1

HCID 22745278HCID 22745278, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Forty-one (41) mg of 1-[1-(piperidin-4-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one.di-trifluoroacetate was dissolved in 5 ml of dichloromethane, and to which 25 mg of diisopropylethylamine and 11 mg of ethyl chloroformate were added, followed by stirring overnight. The reaction mixture was distributed between chloroform and saturated aqueous sodium bicarbonate solution. The organic layer was dried over sodium sulfate, concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol=10/1). Thus 22 mg of the title compound was obtained as a colorless, amorphous substance.

Workup

  1. dry with materialThe organic layer was dried over sodium sulfate
  2. concentrationconcentrated
  3. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-6937df9d37f548408df6e1ac1e544ea5
Source dataset
uspto-grants-2004_03
Patent number
US06699880B1

Reaction notes

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