Hydrochloric Acid → 3-[(1S)-1-Aminoethyl]benzonitrile

HRID 2300768Notes

Reaction equation

HRID 2300768 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C@@H:9]([N:11]=[N+]=[N-])[CH3:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>C1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([C@@H:9]([NH2:11])[CH3:10])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11776TriphenylphosphineHCID 867587533-[(1S)-1-Azidoethyl]benzonitrile

Product 1

HCID 210652103-[(1S)-1-Aminoethyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

(S)-1-(3-cyanophenyl)-1-azidoethane (1.42 mmol) was dissolved in benzene (4 mL), H2O (500 μL) was added followed by triphenylphosphine (2.90 mmol). The resultant mixture was heated to 80° C. for 3.5 h. 25 mL of 2N HCl was added and the mixture washed 3×20 mL diethyl ether. These washes were discarded and the aqueous phase made strongly basic by the addition of 5N NaOH. This basic aqueous phase was then extracted 3×25 mL diethyl ether, these extracts combined, washed with brine, dried (MgSO4) and concentrated under reduced pressure. The residue was used without further purification (150 mg). 1H NMR (500 MHz, CDCl3): δ 7.70 (m, 1H); 7.62 (d, J=7.8 Hz, 1H); 7.54 (m, 1H); 7.44 (t, J=7.8 Hz, 1H); 4.20 (q, J=6.6 Hz, 1H); 1.40 (d, J=6.6 Hz, 3H).

Workup

  1. washthe mixture washed 3×20 mL diethyl ether
  2. additionthe aqueous phase made strongly basic by the addition of 5N NaOH
  3. extractionThis basic aqueous phase was then extracted 3×25 mL diethyl ether
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was used without further purification (150 mg)

Sources & evidence

ORD record
ord-0efc812ee1c14b728233420600af9dcf
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

Loading…