Formaldehyde → HCID 53726018, compound

HRID 414201Notes

Reaction equation

HRID 414201 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][CH2:14][CH:15]([OH:36])[CH2:16][O:17][C:18]2[CH:35]=[CH:34][CH:33]=[CH:32][C:19]=2[C:20]([NH:22][C:23]2[CH:31]=[CH:30][CH:29]=[C:28]3[C:24]=2[CH:25]=[CH:26][NH:27]3)=[O:21])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C=O.[C:39]([BH3-])#N.[Na+].[OH-].[Na+]>CO.[Cl-].[Zn+2].[Cl-].O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH3:39])[CH2:14][CH:15]([OH:36])[CH2:16][O:17][C:18]2[CH:35]=[CH:34][CH:33]=[CH:32][C:19]=2[C:20]([NH:22][C:23]2[CH:31]=[CH:30][CH:29]=[C:28]3[C:24]=2[CH:25]=[CH:26][NH:27]3)=[O:21])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 20098373HCID 20098373, compound

Product 1

HCID 53726018HCID 53726018, compoundYield 72.9%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

Under an inert atmosphere, a solution of 0.2 g of 2[3-[[2-(3,4-dimethoxyphenyl)ethyl]amino]-2-hydroxypropoxy]-N-(1H-indol-4-yl)-benzamide in 5 ml of methanol in the presence of 0.1 ml of formaldehyde with 40% of water was admixed with a solution of 26 mg of sodium cyanoborohydride and 27.2 mg of zinc chloride in 5 ml of methanol and the reaction mixture was left for 2 hours at ambient temperature. 5 ml of 0.1N sodium hydroxide were added, and the mixture was extracted with ethyl acetate. The organic phase was washed with water, dried, and the solvents were eliminated under reduced pressure to obtain 0.230 g of crude product. It was purified by chromatography over silica (eluent: chloroform--ethyl acetate--triethylamine, 6-3-1) to obtain 0.150 g of 2-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]-2-hydroxypropoxy]-N-(1H-indol-4-yl)-benzamide

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. customdried
  4. customto obtain 0.230 g of crude product
  5. customIt was purified by chromatography over silica (eluent: chloroform--ethyl acetate--triethylamine, 6-3-1)

Sources & evidence

ORD record
ord-10399656b5594d75bbad6188e2bcf6a2
Source dataset
uspto-grants-1988_12
Patent number
US04791109

Reaction notes

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