Methylamine → N-(2'-Cyanobiphenyl-4-yl)methyl-N-methyl amine

HRID 1450368Notes

Reaction equation

HRID 1450368 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]#[N:16])=[CH:5][CH:4]=1.[CH3:17][NH2:18]>C1COCC1>[C:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][NH:18][CH3:17])=[CH:4][CH:5]=1)#[N:16]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 15019124'-(Bromomethyl)-2-cyanobiphenyl

Product 1

HCID 15337416N-(2'-Cyanobiphenyl-4-yl)methyl-N-methyl amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

62.1 g (228 mmol) 4-bromomethyl-2'-cyanobiphenyl (prepared according to D. J. Carini et al., J. Med. Chem. 1992, 34, 2525) were dissolved in 3 l THF. After addition of 1.5 l of a 40% aqueous solution of methylamine the mixture was stirred over night at room temperature, and the THF distilled off in vacuo. The remaining aqueous layer was extracted with ethyl acetate, the extract dried by stirring over night with 0.4 nm mole sieve, and evaporated in vacuo. The title compound was obtained as a viscous oil, which was pure enough according to its 1H-NMR spectrum for further conversions,

Workup

  1. distillationthe THF distilled off in vacuo
  2. extractionThe remaining aqueous layer was extracted with ethyl acetate
  3. customthe extract dried
  4. stirringby stirring over night with 0.4 nm mole sieve
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-9027e80bd6ee40c583207b1dff186aa0
Source dataset
uspto-grants-1997_02
Patent number
US05602137

Reaction notes

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