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

HRID 4574

Reaction equation

HRID 4574 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 amide 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-637be44371d74ee394c7fcecade573e7
Source dataset
uspto-grants-1988_02
Patent number
US04727079

Linked notes

Loading…