Diethyl Ether → 3-[(Dimethylamino)methyl]-N,N-dimethyl-1H-indole-5-ethanesulphonamide

HRID 982007Notes

Reaction equation

HRID 982007 reaction equation
[CH3:1][N:2]([CH3:17])[S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2)(=[O:5])=[O:4].[Cl-].C[CH:20]=[N+:21]=[CH:22]C.[CH3:24]COCC>C(#N)C>[CH3:20][N:21]([CH2:22][C:11]1[C:10]2[C:14](=[CH:15][CH:16]=[C:8]([CH2:7][CH2:6][S:3]([N:2]([CH3:1])[CH3:17])(=[O:5])=[O:4])[CH:9]=2)[NH:13][CH:12]=1)[CH3:24]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 13475761N,N-Dimethyl-1H-indole-5-ethanesulphonamideHCID 21873455N,N-dimethylmethylene ammonium chloride

Product 1

HCID 134757383-[(Dimethylamino)methyl]-N,N-dimethyl-1H-indole-5-ethanesulphonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of the product of Stage (ii) (0.8 g) in acetonitrile (40 ml) containing N,N-dimethylmethyleneammonium chloride (0.6 g) was stirred at room temperature for 3 h. The resulting solution was partitioned between sodium carbonate (2N, 50 ml) and ethyl acetate (2×50 ml). The organic extracts were dried (Na2SO4) and evaporated in vacuo to give a solid. Trituration with ether gave the title compound as a solid (0.9 g) m.p. 156°-159°.

Workup

  1. customThe resulting solution was partitioned between sodium carbonate (2N, 50 ml) and ethyl acetate (2×50 ml)
  2. dry with materialThe organic extracts were dried (Na2SO4)
  3. customevaporated in vacuo
  4. customto give a solid

Sources & evidence

ORD record
ord-eea0b1883570444d948d57c5ea794e03
Source dataset
uspto-grants-1991_02
Patent number
US04994483

Reaction notes

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