4-Piperidinecarboxylic acid → 2-(piperidin-4-yl)-1H-1,3-benzodiazole

HRID 1913143Notes

Reaction equation

HRID 1913143 reaction equation
[C:1]1([NH2:8])[C:2]([NH2:7])=[CH:3][CH:4]=[CH:5][CH:6]=1.[NH:9]1[CH2:14][CH2:13][CH:12]([C:15](O)=O)[CH2:11][CH2:10]1.[OH-].[Na+]>Cl>[NH:9]1[CH2:14][CH2:13][CH:12]([C:15]2[NH:8][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=3[N:7]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 37734-Piperidinecarboxylic acidHCID 7243O-PhenylenediamineHCID 14798Sodium Hydroxide

Product 1

HCID 7158102-(piperidin-4-yl)-1H-1,3-benzodiazoleYield 38%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

This compound is synthesized as described by adaptation of the following reference: J. Heterocyclic Chem., 1989, 26, 54. A mixture of benzene-1,2-diamine (12.6 g, 116 mmol), piperidine-4-carboxylic acid (15 g, 116 mmol) and 4M aqueous HCl (250 mL) is stirred and heated under reflux for 48 h. The reaction mixture is cooled to room temperature and is made basic by addition of 5M aqueous NaOH. The precipitate formed is collected by suction filtration, washed with water and dried in the vacuum oven to afford 8.8 g (38%) of 2-(piperidin-4-yl)-1H-benzimidazole. m/z=202 [M++H].

Workup

  1. customThis compound is synthesized
  2. temperatureheated
  3. temperatureunder reflux for 48 h
  4. customThe precipitate formed
  5. filtrationis collected by suction filtration
  6. washwashed with water
  7. customdried in the vacuum oven

Sources & evidence

ORD record
ord-928d8aeccbed413496fc2d1e4e3f0f88
Source dataset
uspto-grants-2013_12
Patent number
US08609696B2

Reaction notes

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