Trimethylphosphine → 3-(Aminomethyl)-5-(trifluoromethyl)benzonitrile

HRID 2075071Notes

Reaction equation

HRID 2075071 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:8]#[N:9])=[N+]=[N-].CP(C)C>C1COCC1>[NH2:1][CH2:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:12]=1)[C:8]#[N:9]

Participants

4

Reactant 2

HCID 68983TrimethylphosphineHCID 866150523-Azidomethyl-5-trifluoromethyl-benzonitrile

Product 1

HCID 451158403-(Aminomethyl)-5-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-azidomethyl-5-trifluoromethyl-benzonitrile (140 mg, 0.619 mmol) in THF (1 ml) was treated with trimethyl phosphine (94.2 mg, 1.24 mmol) at room temperature and stirred for 2 hours. Reaction was quenched with water and stirred for 30 minutes. Reaction was extracted with ethyl ether and organic layer was dried over anhydrous magnesium sulphate and concentrated in vacuo. The crude product (70 mg, 56%) was used without further purification. 1H NMR (400 MHz, CDCl3) δ ppm 1.64 (s, 2H) 3.98 (s, 2H) 7.74 (s, 1H) 7.83 (s, 2H).

Workup

  1. customReaction
  2. customwas quenched with water
  3. stirringstirred for 30 minutes
  4. customReaction
  5. extractionwas extracted with ethyl ether and organic layer
  6. dry with materialwas dried over anhydrous magnesium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe crude product (70 mg, 56%) was used without further purification

Sources & evidence

ORD record
ord-195abeb94bb544ab909048d5ecf32f93
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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