Methylamine → N-Methyl-1-(2-methylphenyl)methanamine

HRID 268642Notes

Reaction equation

HRID 268642 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10][NH2:11].[BH4-].[Na+]>CO>[CH3:10][NH:11][CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 107222-MethylbenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 263103N-Methyl-1-(2-methylphenyl)methanamineYield 93.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2-methylbenzaldehyde (10.0 g, 83.23 mmol) in MeOH at 25° C. was added methylamine (40 % in H2O, 25.85 g, 332.9 mmol). The reaction mixture was stirred at 25° C. for 30 min after which time it was cooled to 0° C. and NaBH4 (6.30 g, 166.5 mmol) was added portion-wise. The reaction mixture was then warmed to 25° C. and stirred for an additional 1 hr. The solvent was removed under reduced pressure and water and CH2Cl2 were added. The organic layer was separated and washed with saturated NaHCO3 and brine. After drying over Na2SO4, organic phase was concentrated to afford desired methyl-(2-methyl-benzyl)-amine (10.49 g, 93.2%) as an oil of sufficient purity for use in the next reaction: MS(APCI+) 136.3 m/z (M+H); H-NMR (CDCl3) δ 7.35-7.08 (m, 3 H), 3.73 (s, 2 H), 2.49 (s, 3 H), 2.34 (s, 3 H).

Workup

  1. temperaturewas cooled to 0° C.
  2. temperatureThe reaction mixture was then warmed to 25° C.
  3. stirringstirred for an additional 1 hr
  4. customThe solvent was removed under reduced pressure and water and CH2Cl2
  5. additionwere added
  6. customThe organic layer was separated
  7. washwashed with saturated NaHCO3 and brine
  8. dry with materialAfter drying over Na2SO4, organic phase
  9. concentrationwas concentrated

Sources & evidence

ORD record
ord-b241f0bea98e4d75ad7a00c3b9f138bd
Source dataset
uspto-grants-2008_11
Patent number
US07446121B2

Reaction notes

Loading…