Methanol → Hordenine

HRID 1844254Notes

Reaction equation

HRID 1844254 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7]Br)=[CH:4][CH:3]=1.[CH3:11][NH2:12].[CH3:13]O>>[CH3:11][N:12]([CH3:13])[CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 6329MethylamineHCID 842214-(2-Bromoethyl)phenol

Product 1

HCID 68313HordenineYield 92%

Procedure

To 250 mg of 4-hydroxyphenethyl bromide in a round-bottomed flask, a 10 M excess of methylamine (6.22 mL of 2M in MeOH) was added and the solution was stirred at r.t. overnight. After filtration, the solvent was evaporated and gave the product in crystalline form in 92% yield, 0.23 g, light yellow. m.p.: 73-76° C. TLC (EtAc:MeOH, 9:1 v/v): RF=0.1. 1H NMR, δ: 9.43 (s, 1H), 7.12 (d, 2H), 6.70 (d, 2H), 2.74 (m, 4H), 2.30 (s, 6H). 13C NMR, δ: 167.5, 134.3, 130.2, 115.6, 60.6, 45.9, 32.4. Anal. calcd for C10H15NO: C, 72.69; H, 9.15; N, 8.48%. Found; C, 72.60; H, 9.30; N, 8.40%.

Workup

  1. filtrationAfter filtration
  2. customthe solvent was evaporated
  3. customgave the product in crystalline form in 92% yield, 0.23 g

Sources & evidence

ORD record
ord-89111cb4ebe1466e96e58393d9cf34c8
Source dataset
uspto-grants-2015_02
Patent number
US08946302B2

Reaction notes

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