Methylamine → N-Methyltyramine

HRID 1844253Notes

Reaction equation

HRID 1844253 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]>CO>[CH3:11][NH:12][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 842214-(2-Bromoethyl)phenol

Product 1

HCID 9727N-MethyltyramineYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 250 mg of 4-hydroxyphenethyl bromide in a round-bottomed flask, a 10 M excess of MeNH2 (6.2 mL of 2M in MeOH) was added and the solution was stirred at r.t. overnight. After filtration, the solvent was removed to give a brown oil in 80% yield. TLC (EtAc:MeOH, 9:1 v/v): RF=0.33. 1H NMR, δ: 9.42 (s, 1H), 7.10 (d, 2H), 6.75 (d, 2H), 3.60 (s, 3H), 2.84 (t, 2H), 2.60 (t, 2H), 1.90 (s, 1H). 13C NMR, δ: 167.5, 131.2, 128.3, 112.4, 41.5, 36.4, 35.0. Anal. calcd for C9H13NO: C, 71.49; H, 8.67; N, 9.26%. Found; C, 71.50; H, 8.80; N, 9.20%.

Workup

  1. filtrationAfter filtration
  2. customthe solvent was removed
  3. customto give a brown oil in 80% yield

Sources & evidence

ORD record
ord-db41d30292b94e60b58ee7ca4d36a973
Source dataset
uspto-grants-2015_02
Patent number
US08946302B2

Reaction notes

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