Sodium Hydroxide → N-Methyltyramine

HRID 1015920Notes

Reaction equation

HRID 1015920 reaction equation
[OH-].[Na+].Br.[CH3:4][NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1>CO>[CH3:4][NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 223241464-[2-(Methylamino)ethyl]phenol--hydrogen bromide (1/1)

Product 1

HCID 9727N-Methyltyramine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In a separate reaction vessel, a mixture of sodium hydroxide (0.603 Kg) and methanol (3.18 Kg) was stirred until the sodium hydroxide was completely dissolved and then N-methyl-N-(2-[4-hydroxyphenyl]ethyl) amine HBr salt (A12 HBr) (1 kg, by assay) in methanol (1.58 Kg) was added under an atmosphere of nitrogen. After stirring, the above mixture was concentrated to provide N-methyl-N-(2-[4-hydroxyphenyl]ethyl) amine as a slurry. The solution was cooled to about 5° C. under an atmosphere of nitrogen and then stirred for about 0.5 hours.

Workup

  1. customIn a separate reaction vessel
  2. dissolutionwas completely dissolved
  3. concentrationthe above mixture was concentrated

Sources & evidence

ORD record
ord-e8ad31f60ee14d8882ba6b3fa3d0f023
Source dataset
uspto-grants-2011_07
Patent number
US07985879B2

Reaction notes

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