3-Methoxytyramine → 1-Methyl-3-{N-[beta-(4-hydroxy-3-methoxyphenyl)ethyl]}carbamoylpyridinium iodide

HRID 1638853Notes

Reaction equation

HRID 1638853 reaction equation
C[I:2].[I-].[CH3:4][N+:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11](=[O:23])[NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([OH:22])[CH:16]=2)[CH:6]=1.[CH3:24]OC1C=C(C=CC=1O)CCN>>[I-:2].[CH3:4][N+:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11](=[O:23])[NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([O:22][CH3:24])[CH:16]=2)[CH:6]=1

Participants

4

Reactant 3

HCID 16693-MethoxytyramineHCID 6328Methyl iodideHCID 134734211-Methyl-3-{N-[beta-(3,4-dihydroxyphenyl)ethyl]carbamoyl}pyridinium iodide

Product 1

HCID 140504251-Methyl-3-{N-[beta-(4-hydroxy-3-methoxyphenyl)ethyl]}carbamoylpyridinium iodide

Procedure

N-nicotinoyl-3-methoxytyramine was prepared by following the procedure used for the preparation of compound 7. The isolated crude amine was quaternized directly with methyl iodide following the method used for the preparation of compound 6a. Crystallization from methanol gave a yellow crystalline compound, m.p. 192°-194° C. with overall yield of 84%, calculated on the basis of 3-methoxytyramine starting material. NMR (D2O) closely similar to that of 6a except for the singlet at δ 3.66 for OCH3.

Workup

  1. customCrystallization from methanol
  2. customgave a yellow crystalline compound, m.p. 192°-194° C. with overall yield of 84%

Sources & evidence

ORD record
ord-64ab05d2307646ae86d899657c6a44e0
Source dataset
uspto-grants-1989_11
Patent number
US04880921

Reaction notes

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