1-Butanol → N-(Piperidin-4-ylmethyl)-1H-benzo[d]imidazol-2-amine

HRID 2109988Notes

Reaction equation

HRID 2109988 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.O1CCOCC1.Cl.[OH-].[Na+].C(O)CCC>CO>[NH:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[NH:15][CH2:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 14798Sodium HydroxideHCID 204431481,4-Dioxane hydrochlorideHCID 21912578tert-butyl 4-[(1H-benzimidazol-2-ylamino)methyl]piperidine-1-carboxylate

Product 1

HCID 11481631N-(Piperidin-4-ylmethyl)-1H-benzo[d]imidazol-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After dissolving 4-[(1H-benzimidazol-2-ylamino)-methyl]-piperidine-1-carboxylic acid tert-butyl ester (4.33 g, 13.1 mmol) in methanol (10 mL), a 4N hydrogen chloride-1,4-dioxane solution (33 mL, 131 mmol) was added in small portions at a time in an ice bath, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was cooled on ice, 2N aqueous sodium hydroxide was added to adjust the pH to approximately 11. Salt was added to the aqueous solution to saturation, and the organic layer obtained by extraction with 1-butanol (100 mL×3 times) was washed with saturated brine and then dried over anhydrous sodium sulfate. The dried 1-butanol was concentrated under reduced pressure to obtain (1H-benzimidazol-2-yl)-piperidin-4-ylmethyl-amine.

Workup

  1. additionwas added
  2. additionSalt was added to the aqueous solution to saturation
  3. washwas washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe dried 1-butanol was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c89846ea5cbd4e13b0d8a29646ea76ab
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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