Acetone → HCID 19734242, compound

HRID 327079Notes

Reaction equation

HRID 327079 reaction equation
O.[NH2:2][CH2:3][CH:4]1[C:10]2=[CH:11][NH:12][C:13]3[CH:14]=[CH:15][CH:16]=[C:8]([C:9]=32)[C:7](=[O:17])[NH:6][CH2:5]1.[CH3:18][C:19]([CH3:21])=O>O1CCCC1>[CH:19]([NH:2][CH2:3][CH:4]1[C:10]2=[CH:11][NH:12][C:13]3[CH:14]=[CH:15][CH:16]=[C:8]([C:9]=32)[C:7](=[O:17])[NH:6][CH2:5]1)([CH3:21])[CH3:18]

Participants

4

Reactant 2

HCID 180AcetoneHCID 19734268HCID 19734268, compound

Product 1

HCID 19734242HCID 19734242, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

0.82 g of borane-dimethylamine complex was added to a stirred solution of 3-aminomethyl-3,4,5,6-tetrahydro-6-oxo-1H-azepino[5,4,3-cd]indole hydrate (see Example 1C for preparation) in 80 ml of tetrahydrofuran. The solution was heated under reflux for 1 hour and subsequently, at a temperature of 45° C., 10 ml of acetone were added dropwise. The reaction mixture was stirred at a temperature of 60° C. for 2.5 hours. To work up the reaction mixture it was subsequently evaporated to dryness, and the residue was dissolved in a mixture of water and dichloromethane. The dichloromethane phase was separated, and the aqueous phase was extracted three more times with 50 ml portions of a 9:1 dichloromethane/methanol mixture. The organic phases were combined and evaporated to dryness. The crude product which remained as residue was purified by chromatography under slightly elevated pressure (=flash chromatography) on silica gel using methanol/ethyl acetate 4:1 as eluent. The title compound was obtained as an oil.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 1 hour
  3. customwas subsequently evaporated to dryness
  4. dissolutionthe residue was dissolved in a mixture of water and dichloromethane
  5. customThe dichloromethane phase was separated
  6. extractionthe aqueous phase was extracted three more times with 50 ml portions of a 9:1 dichloromethane/methanol mixture
  7. customevaporated to dryness
  8. customwas purified by chromatography under slightly elevated pressure (=flash chromatography) on silica gel

Sources & evidence

ORD record
ord-67c7e4af48a04013966617b5d861532f
Source dataset
uspto-grants-1993_12
Patent number
US05272143

Reaction notes

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