Formaldehyde → 1-(Pyrrolidin-1-ylmethyl)benzimidazole

HRID 591838Notes

Reaction equation

HRID 591838 reaction equation
N1C2C=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=N1.OCCN1CCN(C2C=CC([C:25]3[NH:34][C:33](=O)[C:32]4[C:27](=[CH:28][C:29](OC)=[CH:30][C:31]=4OC)[N:26]=3)=CC=2)CC1.C=O>O>[N:3]1([CH2:33][N:34]2[C:32]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[N:26]=[CH:25]2)[CH2:4][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 1359391212-(4-(4-(2-hydroxyethyl)piperazin-1-yl)phenyl)-5,7-dimethoxyquinazolin-4(3H)-oneHCID 178418385HCID 178418385, compound

Product 1

HCID 2090961-(Pyrrolidin-1-ylmethyl)benzimidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 1H-benzotriazole (10.0 g, 83.9 mmol) in water (84 mL) was added pyrrolidine 2 (6.3 mL, 226.6 mmol). After 10 minutes of vigorous stirring at room temperature, formaldehyde 37% aqueous solution was added. The reaction mixture was stirred for 1 hour, then the precipitate was filtered off, and washed with water to afford 1-pyrrolidin-1-ylmethyl-1H-benzoimidazole as an off-white solid. Yield: 14.58 g (85.9%).

Workup

  1. stirringThe reaction mixture was stirred for 1 hour
  2. filtrationthe precipitate was filtered off
  3. washwashed with water

Sources & evidence

ORD record
ord-7fa88af7c63d408f97cb9b78982fcb9e
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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