Methylamine → 2-Bromo-N-methylbenzylamine

HRID 1977489Notes

Reaction equation

HRID 1977489 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10][NH2:11].[BH4-].[Na+]>C1COCC1>[CH3:10][NH:11][CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[Br:1]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 811292-BromobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 5223602-Bromo-N-methylbenzylamineYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

29.4 g of o-Bromobenzaldehyde and 81 ml of aqueous, 40% methylamine solution are combined with 238 ml of THF and at RT 19 g of NaBH4 are added in batches within 25 minutes. The mixture is left to stand overnight at RT, concentrated using a rotary evaporator, and the residue is stirred into ice water. The aqueous phase is extracted twice with ether and the combined ether phases are evaporated down under reduced pressure. After chromatography on silica gel with ethyl acetate or ethyl acetate/methanol (4:1) as eluant, 18.5 g of N-methyl-2-bromobenzylamine (a) are obtained in the form of a yellowish liquid. Yield: 58%.

Workup

  1. additionare added in batches within 25 minutes
  2. waitThe mixture is left
  3. concentrationconcentrated
  4. customa rotary evaporator
  5. extractionThe aqueous phase is extracted twice with ether
  6. customthe combined ether phases are evaporated down under reduced pressure

Sources & evidence

ORD record
ord-91ca148930ed4d8fa0b64a201b95cf33
Source dataset
uspto-grants-2001_05
Patent number
US06232468B1

Reaction notes

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