Methylamine → 3-Methoxy-N-methylbenzylamine

HRID 1749202

Reaction equation

HRID 1749202 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[CH3:11][NH2:12].[BH4-].[Na+]>CO>[CH3:9][O:8][C:4]1[CH:3]=[C:2]([CH2:1][NH:12][CH3:11])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 115693-MethoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 51522253-Methoxy-N-methylbenzylamineYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of m-anisaldehyde (205 g, 1.5 mol) in methanol (800 mL) at room temperature was added methylamine (130 mL of 40% in water, 1.5 mol). The resulting solution was cooled to 0° C. and sodium borohydride (83 g, 2.3 mol) was added in batches. The reaction solution was stirred at 0° C. for 2 h, then warmed to room temperature, concentrated in vacuo and diluted with water. The organic phase was separated, diluted with ethyl acetate, washed with 1:1 water/brine, dried over sodium sulfate and concentrated in vacuo to give the desired benzylamine (158.5 g, 70%) as a clear oil. The combined aqueous extracts were extracted with dichloromethane (3×). The combined methylene chloride extracts were washed with 1:1 water/brine, dried over sodium sulfate and concentrated in vacuo to give additional benzylamine (66.7 g, 29%) as a clear oil: 1H NMR (300 MHz, CDCl3) 7.24 (t, J=8.4 Hz, 1H), 6.91-6.78 (m, 3H), 3.81 (s, 3H), 3.73 (s, 2H), 2.46 (s, 3H).

Workup

  1. temperaturewarmed to room temperature
  2. concentrationconcentrated in vacuo
  3. additiondiluted with water
  4. customThe organic phase was separated
  5. additiondiluted with ethyl acetate
  6. washwashed with 1:1 water/brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09917f9828c949d4bfc74bd611024190
Source dataset
uspto-grants-2015_10
Patent number
US09156812B2

Linked notes

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