Hydrochloric Acid → HCID 21273251, compound

HRID 1382791Notes

Reaction equation

HRID 1382791 reaction equation
[CH3:1][N:2]([CH3:13])[C:3](=[O:12])[CH2:4][CH2:5][C:6]1[N:7]=[CH:8][NH:9][C:10]=1[CH3:11].[ClH:14]>C(O)C>[ClH:14].[ClH:14].[CH3:13][N:2]([CH3:1])[C:3](=[O:12])[CH2:4][CH2:5][C:6]1[N:7]=[CH:8][NH:9][C:10]=1[CH3:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21273212HCID 21273212, compound

Product 1

HCID 21273251HCID 21273251, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N,N-dimethyl-3-(5-methyl-1H-imidazol-4-yl)-1-propanamide (300 mg) in ethanol (15 ml) was acidified (to pH 1) by the addition of ethanolic hydrogen chloride, and evaporated to yield an oil which was triturated with ether to give N,N-dimethyl-3-(5-methyl-1H-imidazol-4-yl)-1-propanamide dihydrochloride (270 mg) as a powder. This was added to a mixture of 1,7-dimethylindole (195 mg) and phosphorus oxychloride (0.15 ml) and the mixture was heated at 85° in a `closed vessel` for 1.5 h. The mixture was cooled, cold water (50 ml) was added and the suspension was stirred for 0.5 h. It was then washed with ethyl acetate (2×40 ml; discarded), basified with 2N sodium carbonate and extracted with ethyl acetate (4×80 ml). The combined, dried organic extracts were evaporated to give the free base of the title compound (232 mg) as a solid which was dissolved in hot ethanol (15 ml), and maleic acid (105 mg) in warm ethanol (5 ml) was added. The solution was evaporated and the residual solid was crystallised from ethanol (15 ml) to give the title compound (235 mg), m.p. 164°-165°.

Workup

  1. customevaporated
  2. customto yield an oil which
  3. customwas triturated with ether

Sources & evidence

ORD record
ord-f17ded3e95804d3cbbc93892a9227285
Source dataset
uspto-grants-1989_02
Patent number
US04808581

Reaction notes

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