Methylamine → 1-(4-fluorophenyl)-N-methylmethanamine

HRID 2181005Notes

Reaction equation

HRID 2181005 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][NH2:11].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:11][CH3:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 680234-FluorobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 7368601-(4-fluorophenyl)-N-methylmethanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 4-fluorobenzaldehyde (2.48 g) in MeOH was added methylamine (40% aqueous solution, 2.0 mL). The reaction mixture was stirred at RT for 12 h at which time NaBH4 (0.38 g) was added. After stirring for 1 h the reaction was quenched with H2O and extracted with ethyl acetate. The combined extracts were dried, filtered, and concentrated to yield (4-fluorobenzyl)-methylamine (2.30 g) which was used without further purification.

Workup

  1. additionwas added
  2. customwas quenched with H2O
  3. extractionextracted with ethyl acetate
  4. customThe combined extracts were dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b295f0fb80b5426b9728b2411e217aa5
Source dataset
uspto-grants-2005_05
Patent number
US06890938B2

Reaction notes

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