Methylamine → HCID 20121408, compound

HRID 901072Notes

Reaction equation

HRID 901072 reaction equation
[CH3:1][NH2:2].Br[CH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[F:13]>C(O)C.ClCCl>[C:9]([C:8]1[CH:11]=[CH:12][C:5]([CH2:4][NH:2][CH3:1])=[C:6]([F:13])[CH:7]=1)#[N:10]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 27831494-(Bromomethyl)-3-fluorobenzonitrile

Product 1

HCID 20121408HCID 20121408, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

1 ml of a 16.5% solution of methanamine in ethanol is cooled by an ice bath and a solution of 120 mg (0.56 mM) of 4-(bromomethyl)-3-fluoro-benzonitrile in 1 ml of dichloromethane is added dropwise. The reaction medium is then agitated for 4 hours at ambient temperature and is then concentrated under reduced pressure. The residue is taken up with ethyl acetate and washed with a solution of sodium bicarbonate. The organic phase is dried over magnesium sulphate and then concentrated under reduced pressure. The crude product is purified by chromatography on silica gel in eluting with the aid of a mixture of dichloromethane/methanol (98/0.05; v/v). The expected amine is thus obtained as a colourless oil (yield=49%).

Workup

  1. concentrationis then concentrated under reduced pressure
  2. washwashed with a solution of sodium bicarbonate
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product is purified by chromatography on silica gel
  6. washin eluting with the aid of a mixture of dichloromethane/methanol (98/0.05; v/v)

Sources & evidence

ORD record
ord-1c199bfe58d446308c7653bcf7e2ca48
Source dataset
uspto-grants-2008_04
Patent number
US07361687B2

Reaction notes

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