Formaldehyde → HCID 18509858, compound

HRID 1370143Notes

Reaction equation

HRID 1370143 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[CH2:5][N:6]1[C:10]2[CH:11]=[C:12]([C:15]#[N:16])[CH:13]=[CH:14][C:9]=2[N:8]([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[C:7]1=[O:23].C=O.[B-][C:32]#N.[Na+].C(=O)(O)[O-].[Na+]>CO.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[CH2:5][N:6]1[C:10]2[CH:11]=[C:12]([C:15]#[N:16])[CH:13]=[CH:14][C:9]=2[N:8]([CH:17]2[CH2:18][CH2:19][N:20]([CH3:32])[CH2:21][CH2:22]2)[C:7]1=[O:23]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 18509673HCID 18509673, compoundHCID 20587905Sodium cyanoborohydride [MI]

Product 1

HCID 18509858HCID 18509858, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 3-(3-chloro-4-methoxybenzyl)-1-(piperidin-4-yl)-5-cyano-2,3-dihydro-1H-benzimidazole-2-one (91 mg) in methanol (5 mL) were added 37% formaldehyde aqueous solution (220 mg), sodium cyanotrihydroborate (43.2 mg) and acetic acid (5 drops) under nitrogen at ambient temperature. After stirring for 2 hours at same temperature, the reaction mixture was poured into saturated sodium bicarbonate solution and extracted with chloroform. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diethyl ether to give 3-(3-chloro-4-methoxybenzyl)-5-cyano-1-(1-methylpiperidin-4-yl)-2,3-dihydro-1H-benzimidazole-2-one (75 mg) as an amorphous powder.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-e568e51c319e44ba9ba0e38805c3e17d
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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