Dimethylformamide → HCID 19734223, compound

HRID 327083Notes

Reaction equation

HRID 327083 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][N:19]([CH3:22])[CH:20]=O>>[CH3:18][N:19]([CH:22]=[N: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)[CH3:20]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 19734268HCID 19734268, compound

Product 1

HCID 19734223HCID 19734223, compound

Procedure

1 g of 3-aminomethyl-3,4,5,6-tetrahydro-6-oxo-1H-azepino[5,4,3-cd]indole hydrate (see Example 1C for preparation) was dissolved in 10 ml of dimethylformamide at room temperature. 1 g of N-chloromethylene-N,N-dimethyliminium chloride was added to this solution. The reaction mixture was subsequently stirred at room temperature for 2 hours. To work up the reaction mixture it was evaporated under reduced pressure (water pump vacuum) and the residue was taken up in a mixture of equal parts of water and ethyl acetate. The aqueous phase was adjusted to a pH of 8.5 by adding saturated sodium bicarbonate solution, then the organic phase was separated and the aqueous phase was extracted three times more with 50 ml portions of ethyl acetate. The combined organic extracts were concentrated to 25 ml. The solution of the title compound obtained in this way was further worked up as described in Example 15. 0.5 g of 3-(dimethylaminomethylideneamino-methyl)-3,4,5,6-tetrahydro-6-oxo-1H-azepino[5,4,3-cd]indole hydrochloride was obtained with a melting point of 178° to 179° C.

Workup

  1. customwas evaporated under reduced pressure (water pump vacuum)
  2. additionthe residue was taken up in a mixture of equal parts of water and ethyl acetate
  3. additionby adding saturated sodium bicarbonate solution
  4. customthe organic phase was separated
  5. extractionthe aqueous phase was extracted three times more with 50 ml portions of ethyl acetate
  6. concentrationThe combined organic extracts were concentrated to 25 ml

Sources & evidence

ORD record
ord-66b42765636f4073b15d5462eede4a64
Source dataset
uspto-grants-1993_12
Patent number
US05272143

Reaction notes

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