Formaldehyde → HCID 57703902, compound

HRID 1472208Notes

Reaction equation

HRID 1472208 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[C:6]([NH:17][CH2:18][CH2:19][O:20][CH3:21])[CH:5]=1.C=O.[BH3-][C:26]#N.[Na+]>C(O)(=O)C.CO>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15]2)=[C:6]([N:17]([CH2:18][CH2:19][O:20][CH3:21])[CH3:26])[CH:5]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 57703893HCID 57703893, compound

Product 1

HCID 57703902HCID 57703902, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 170 mg of 3-(2-methoxy-ethylamino)-4-(4-methyl-piperazin-1-yl)-benzoic acid methyl ester (0.55 mmol, 1 eq.) in 5 mL of acetic acid were added 3 mL of aqueous solution of formaldehyde and the resulting mixture stirred for 10 minutes at room temperature; a solution of NaCNBH3 (680 mg, 11 mmol, 20 eq.) in 3 mL of MeOH was then added at 0° C. and the solution stirred for 5 minutes. The solvent was removed and the crude washed with water and dichloromethane. The combined organic layers were evaporated and the crude was purified by flash column chromatography, using dichloromethane-methanol 95:5 as eluant, affording 150 mg of the desired product.

Workup

  1. stirringthe solution stirred for 5 minutes
  2. customThe solvent was removed
  3. washthe crude washed with water and dichloromethane
  4. customThe combined organic layers were evaporated
  5. customthe crude was purified by flash column chromatography

Sources & evidence

ORD record
ord-cefb35b8a53f43d6adc8898e979ec22b
Source dataset
uspto-grants-2015_04
Patent number
US09012487B2

Reaction notes

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