Methyl iodide → 1-Methyl-3-{N-[beta-(3,4-dihydroxyphenyl)ethyl]carbamoyl}pyridinium iodide

HRID 4576Notes

Reaction equation

HRID 4576 reaction equation
[C:1]([NH:9][CH2:10][CH2:11][C:12]1[CH:19]=[CH:18][C:16]([OH:17])=[C:14]([OH:15])[CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH3:20][I:21]>CO>[I-:21].[CH3:20][N+:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:1](=[O:8])[NH:9][CH2:10][CH2:11][C:12]2[CH:19]=[CH:18][C:16]([OH:17])=[C:14]([OH:15])[CH:13]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 6328Methyl iodide2×HCID 13473418N-nicotinoyl dopamine

Product 1

HCID 134734211-Methyl-3-{N-[beta-(3,4-dihydroxyphenyl)ethyl]carbamoyl}pyridinium iodide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2 g (7.7 mmol) of nicotinoyldopamine in 40 ml of dry methanol were added 2.5 g (17.6 mmol) of methyl iodide. The reaction mixture was refluxed with stirring for 6 hours. Methyl iodide (1.5 g, 1.05 mmol) was added and refluxing was continued overnight. Methanol was removed and ethyl acetate was added, affording yellowish crystals of the desired product. Yield 2.4 g (77%), m.p. 173°-174° C.

Workup

  1. temperatureThe reaction mixture was refluxed
  2. temperaturerefluxing
  3. waitwas continued overnight
  4. customMethanol was removed
  5. additionethyl acetate was added

Sources & evidence

ORD record
ord-04d2f43c51074e648143c6e7a24764f5
Source dataset
uspto-grants-1988_02
Patent number
US04727079

Reaction notes

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