Hydrochloric Acid → HCID 12050311, compound

HRID 2230166Notes

Reaction equation

HRID 2230166 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[NH:3]1.Cl.[C:18]1(=O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[C-:25]#[N:26].[K+]>O>[O:1]=[C:2]1[N:6]([CH:7]2[CH2:8][CH2:9][N:10]([C:18]3([C:25]#[N:26])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:11][CH2:12]2)[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[NH:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7967CyclohexanoneHCID 9032Potassium CyanideHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one

Product 1

HCID 12050311HCID 12050311, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred suspension of 4-(2-keto-1-benzimidazolinyl)piperidine (500 mg, 2.3 mmol) in 2N HCl(1.15 ml, 2.3 mmol) and water(0.5 ml) was added cyclohexanone(0.24 ml, 2.3 mmol) at 0° C. To this mixture was added a solution of KCN(156 mg, 2.4 mmol) in water(0.3 ml) all at once at room temperature. After 17 h stirring at room temperature, the precipitated white solid was collected by filtration, washed with water, and dried under vacuum at 50° C. for 1 h to afford 605 mg of white powder. As this included small amount of starting material amine, this was purified by column chromatography(silica gel: 130 g, CH2Cl2MeOH:30/1 to 20/1) to give 293 mg(39.3%) of white powder, mp199-201° C.

Workup

  1. filtrationthe precipitated white solid was collected by filtration
  2. washwashed with water
  3. customdried under vacuum at 50° C. for 1 h

Sources & evidence

ORD record
ord-5e908127a3424d38a400c627d8698988
Source dataset
uspto-grants-2002_07
Patent number
US06423725B1

Reaction notes

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