Formaldehyde → HCID 21270023, compound

HRID 1194346Notes

Reaction equation

HRID 1194346 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11](=[O:13])[CH3:12])=[C:3]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH2:20]=O.Cl.[CH3:23][NH:24][CH3:25]>C(O)C>[CH3:23][N:24]([CH3:20])[CH2:25][CH2:12][C:11]([C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:2]([CH3:1])[C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 12311893Ethanone, 1-(1-methyl-2-phenyl-1H-indol-3-yl)-

Product 1

HCID 21270023HCID 21270023, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(1-methyl-2-phenyl-1H-indol-3-yl)-1-ethanone (1.0 g), paraformaldehyde (191 mg) and dimethylamine hydrochloride (347 mg) in ethanol (15 ml) was stirred and heated at reflux for 30 h. The mixture was then evaporated and the residue was treated with water (150 ml) and then filtered. The filtrate was brought to pH 10 with 0.88 ammonia solution and the suspension obtained was extracted with ethyl acetate (2×125 ml). The combined organic extracts were washed with water (50 ml), dried and evaporated to leave an oil (997 mg) which was purified by column chromatography eluting with methanol to give an oil (0.50 g). This was dissolved in ether (50 ml) and extracted with 0.5M hydrochloric acid (2×50 ml). The combined acidic extracts were brought to pH 10 with 0.88 ammonia solution and the resulting precipitate was extracted with ethyl acetate (2×70 ml). The combined organic extracts were washed with water (40 ml), dried and evaporated to leave an oil (0.444 g) which was purified by preparative t.l.c. eluting with methanol to give the title compound (0.30 g) as an oil, which was crystallised from light petroleum, m.p. 55°-57°.

Workup

  1. temperatureheated
  2. temperatureat reflux for 30 h
  3. customThe mixture was then evaporated
  4. additionthe residue was treated with water (150 ml)
  5. filtrationfiltered
  6. customthe suspension obtained
  7. extractionwas extracted with ethyl acetate (2×125 ml)
  8. washThe combined organic extracts were washed with water (50 ml)
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-a22d62a551434043afcf94a2de481434
Source dataset
uspto-grants-1989_03
Patent number
US04814344

Reaction notes

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