Ammonia → 2-Amino-2-fluoromethyl-3-(4-methoxyphenyl)propionitrile

HRID 66641Notes

Reaction equation

HRID 66641 reaction equation
[F:1][CH2:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.[Cl-].[NH4+:15].[NH3:16].[C-:17]#N.[Na+]>>[NH2:15][C:3]([CH2:2][F:1])([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[C:17]#[N:16]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 152671761-Fluoro-3-(4-methoxyphenyl)-2-propanone

Product 1

HCID 127681432-Amino-2-fluoromethyl-3-(4-methoxyphenyl)propionitrile

Procedure

A mixture of 1-fluoro-3-(4-methoxyphenyl)-2-propanone (4.1 g, 0.0225 mol), ammonium chloride (1.5 g) and 28% aqueous ammonia (27 ml) is treated with sodium cyanide (1.4 g), and the mixture is stirred at room temperature overnight under nitrogen. The oil which separates is removed and extracted with diethyl ether, and the ethereal extract is washed with ammonia, dried (MgSO4), and filtered. Evaporation of the ether leaves an oily residue which is washed with pentane by decantation. An NMR analysis of the oily residue (4 g) shows that it consists mainly of the required 2-amino-2-fluoromethyl-3-(4-methoxyphenyl)propionitrile.

Workup

  1. customThe oil which separates is removed
  2. extractionextracted with diethyl ether
  3. extractionthe ethereal extract
  4. washis washed with ammonia
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customEvaporation of the ether
  8. customleaves an oily residue which
  9. washis washed with pentane by decantation

Sources & evidence

ORD record
ord-4b2efea3e4a34f0f943d3b66f7028367
Source dataset
uspto-grants-1982_08
Patent number
US04342780

Reaction notes

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