Formaldehyde → HCID 22467612, compound

HRID 1934656Notes

Reaction equation

HRID 1934656 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:23][CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[C:8]([CH:22]=1)[C:9]([NH:11][CH2:12][C:13]1[CH:21]=[CH:20][C:16]2[O:17][CH2:18][O:19][C:15]=2[CH:14]=1)=[O:10])([O-:3])=[O:2].C=O.[C:32]([BH3-])#N.[Na+]>CO.C(O)(=O)C>[CH3:32][N:27]1[CH2:28][CH2:29][CH:24]([NH:23][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:22][C:8]=2[C:9]([NH:11][CH2:12][C:13]2[CH:21]=[CH:20][C:16]3[O:17][CH2:18][O:19][C:15]=3[CH:14]=2)=[O:10])[CH2:25][CH2:26]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 22467525HCID 22467525, compound

Product 1

HCID 22467612HCID 22467612, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 5-nitro-2-(4-piperidinylamino)-N-(1,3-benzodioxol-5-ylmethyl)benzamide (80.0 mg) and 37% formaldehyde solution (192 mg) in methanol (4 mL) were added sodium cyanoborohydride (37.9 mg) and acetic acid (4 drops). After stirring for 2 hours at ambient temperature, the mixture was partitioned between an aqueous saturated sodium bicarbonate solution and chloroform. The organic layer was separated and washed with water and brine. Then, the resultant was dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give 2-(1-methyl-4-piperidinylamino)-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide as yellow powders (65.0 mg).

Workup

  1. customthe mixture was partitioned between an aqueous saturated sodium bicarbonate solution and chloroform
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialThen, the resultant was dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-761ca8837faa42dfa86897dc5e46a6a1
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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