Hydrochloric Acid → 2-[4-(1-Aminoethyl)phenyl]-2-ethylbutanenitrile

HRID 419978Notes

Reaction equation

HRID 419978 reaction equation
[C:1]([C:3]([C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1)([CH2:6][CH3:7])[CH2:4][CH3:5])#[N:2].[Li]C.[BH4-].[Na+].Cl.[OH-].[Na+].[CH3:23]C#N>CO.O.C1COCC1>[NH2:13][CH:12]([C:11]1[CH:10]=[CH:9][C:8]([C:3]([CH2:4][CH3:5])([CH2:6][CH3:7])[C:1]#[N:2])=[CH:15][CH:14]=1)[CH3:23]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 582984684-(1-Cyano-1-ethylpropyl)benzonitrileHCID 178418348HCID 178418348, compound

Product 1

HCID 582984502-[4-(1-Aminoethyl)phenyl]-2-ethylbutanenitrile

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

4-(1-Cyano-1-ethylpropyl)benzonitrile (936 mg, 5.51 mmol) is added to THF (20.0 mL), and the resulting solution is cooled to −78° C. MeLi (3.44 mL, 5.51 mmol) is added, and the solution is stirred for 20 minutes. NaBH4 (208 mg, 5.51 mmol) is mixed in MeOH (20.0 mL) and added to the first solution. The resulting solution is warmed to room temperature and stirred for 1 hour. 1N HCl (50.0 mL) is added followed by 1N NaOH (60.0 mL). The aqueous phase is extracted with EtOAc (4 times 50.0 mL) and the combined organic phases are dried with MgSO4, filtered and concentrated on the rotovaporator. The product is purified by HPLC: Gilson prep pumps, Flow rate: 30 ml/min, Column: Gemini (5u) 21.2×50 mm, Mobile phase: A=water (10 mM NH4CO3) B=MeCN, (528 mg, 2.44 mmol, 44%). 1H NMR (400 MHz, DMSO-D6) δ ppm 0.77 (t, J=7.32 Hz, 6H) 1.22 (d, J=6.45 Hz, 3H) 1.82-2.07 (m, 4H) 3.97 (q, J=6.64 Hz, 1H) 7.32 (d, J=8.40 Hz, 2H) 7.40 (d, J=8.20 Hz, 2H).

Workup

  1. additionadded to the first solution
  2. temperatureThe resulting solution is warmed to room temperature
  3. stirringstirred for 1 hour
  4. extractionThe aqueous phase is extracted with EtOAc (4 times 50.0 mL)
  5. dry with materialthe combined organic phases are dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated on the rotovaporator
  8. customThe product is purified by HPLC

Sources & evidence

ORD record
ord-5c7a39cae4af4ec4b8717e249ee6f268
Source dataset
uspto-grants-2012_01
Patent number
US08093402B2

Reaction notes

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