Benzoyl chloride → HCID 10113677, compound

HRID 1374139Notes

Reaction equation

HRID 1374139 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[NH:19][C:18]3=[O:26])[CH2:13][CH2:12]2)[CH2:5][CH2:4]1.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(C(C)C)CC)(C)C.N1CCCCC1>C(Cl)(Cl)Cl>[C:27]([N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[NH:19][C:18]3=[O:26])[CH2:13][CH2:12]2)[CH2:5][CH2:4]1)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 21076287HCID 21076287, compound

Product 1

HCID 10113677HCID 10113677, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 20 mg of 1-[1-[2-(piperidin-4-yl)ethyl]piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one dihydrochloride which was synthesized in Production Example 1, 10 mg of benzoyl chloride, 27 mg of diisopropylethylamine and 2 ml of chloroform were added, and sonicated for 30 minutes. Then 20 mg of piperidine was added to the system followed by 10 minutes' standing. The resulting reaction mixture was concentrated, and the residue was purified on silica gel chromatography (chloroform/methanol=15/1) to provide 14 mg of the title compound as a colorless oil.

Workup

  1. additionwere added
  2. customsonicated for 30 minutes
  3. customThe resulting reaction mixture
  4. concentrationwas concentrated
  5. customthe residue was purified on silica gel chromatography (chloroform/methanol=15/1)

Sources & evidence

ORD record
ord-e32869806c084e4485b0eac9fc76e0c2
Source dataset
uspto-grants-2007_01
Patent number
US07164024B2

Reaction notes

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