Water → HCID 19734231, compound

HRID 327077Notes

Reaction equation

HRID 327077 reaction equation
[CH2:1]([NH:8][CH2:9][CH:10]1[C:16]2=[CH:17][NH:18][C:19]3[CH:20]=[CH:21][CH:22]=[C:14]([C:15]=32)[C:13](=[O:23])[NH:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[C:26](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.ClCCl>[CH2:1]([N:8]([CH2:9][CH:10]1[C:16]2=[CH:17][NH:18][C:19]3[CH:20]=[CH:21][CH:22]=[C:14]([C:15]=32)[C:13](=[O:23])[NH:12][CH2:11]1)[CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 19734220HCID 19734220, compound

Product 1

HCID 19734231HCID 19734231, compoundYield 77.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

6.2 g of 3-benzylaminomethyl-3,4,5,6-tetrahydro-6-oxo-1H-azepino[5,4,3-cd]indole (see Example 2 for preparation) were dissolved in 250 ml of dimethylformamide. 0.81 ml of methyl iodide and 1.81 g of potassium carbonate were added to the stirred solution at room temperature. The reaction mixture was stirred at room temperature for 3 hours. Subsequently, to work up, the dimethylformamide was stripped off under reduced pressure (oil pump vacuum) at 50° C. The remaining oily residue was taken up in a mixture of equal parts of water and dichloromethane, the dichloromethane phase was separated, and the aqueous phase was extracted twice more with dichloromethane. The organic phases were combined, dried over sodium sulfate, filtered and evaporated. 3.84 g of oily crude product remained as residue. This was purified by chromatography under moderately elevated pressure (=low pressure chromatography =LPLC under 3 to 6 bar) on silica gel (proprietary product LiChroprep® Si 60) using dichloromethane/methanol 9:1 as eluent. 3.26 g of oily 3-(N-benzyl-N-methylaminomethyl)-3,4,5,6-tetrahydro-6-oxo-1H-azepino[5,4,3-cd]indole were obtained.

Workup

  1. customwas stripped off under reduced pressure (oil pump vacuum) at 50° C
  2. customthe dichloromethane phase was separated
  3. extractionthe aqueous phase was extracted twice more with dichloromethane
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThis was purified by chromatography under moderately elevated pressure (=low pressure chromatography =LPLC under 3 to 6 bar) on silica gel (proprietary product LiChroprep® Si 60)

Sources & evidence

ORD record
ord-ec22b09a2ec1426790db49eb3615eba9
Source dataset
uspto-grants-1993_12
Patent number
US05272143

Reaction notes

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