Sodium Cyanide → 2-Amino-2-fluoromethyl-3-(3,4-dimethoxyphenyl)propionitrile

HRID 66634Notes

Reaction equation

HRID 66634 reaction equation
[F:1][CH2:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1.[Cl-].[NH4+:17].[C-:18]#[N:19].[Na+]>N>[NH2:17][C:3]([CH2:2][F:1])([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1)[C:18]#[N:19]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 205306081-Fluoro-3-(3,4-dimethoxyphenyl)-2-propanone

Product 1

HCID 204871582-Amino-2-fluoromethyl-3-(3,4-dimethoxyphenyl)propionitrile

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

To a suspension of 1-fluoro-3-(3,4-dimethoxyphenyl)-2-propanone (31.5 g, 0.149 mol) and ammonium chloride (9.57 g, 0.179 mol) in a solution of 28% aqueous ammonia (170 ml) is added sodium cyanide (8.77 g, 0.179 mol). The reaction mixture is stirred at room temperature under nitrogen for 20 hours. The solid which separates is removed by filtration on sintered glass, and then washed with 28% aqueous ammonia (50 ml). The solid is dissolved in ether (1.3 l) and the solution is washed with water, then with brine, dried (MgSO4), and filtered. Upon concentration of the solvent, 2-amino-2-fluoromethyl-3-(3,4-dimethoxyphenyl)propionitrile crystallizes (21.8 g), m.p. 76° C.

Workup

  1. customThe solid which separates is removed by filtration on sintered glass
  2. washwashed with 28% aqueous ammonia (50 ml)
  3. dissolutionThe solid is dissolved in ether (1.3 l)
  4. washthe solution is washed with water
  5. dry with materialwith brine, dried (MgSO4)
  6. filtrationfiltered
  7. customUpon concentration of the solvent, 2-amino-2-fluoromethyl-3-(3,4-dimethoxyphenyl)propionitrile crystallizes (21.8 g), m.p. 76° C.

Sources & evidence

ORD record
ord-6e4abbb105384f85bd6f56aa6d216ca3
Source dataset
uspto-grants-1982_08
Patent number
US04342780

Reaction notes

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