Hydrochloric Acid → 2-(4-Isopropylphenyl)propylamine hydrochloride

HRID 1167205Notes

Reaction equation

HRID 1167205 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:13])[C:11]#[N:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].B.CSC.[ClH:18]>O1CCCC1.CO>[ClH:18].[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH3:13])[CH2:11][NH2:12])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 12423031(Dimethyl sulfide)trihydroboronHCID 136820102-[4-(Propan-2-yl)phenyl]propanenitrile

Product 1

HCID 218934972-(4-Isopropylphenyl)propylamine hydrochlorideYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a 100 mL flask, fitted with a condenser, 2-(4-isopropylphenyl)propionitrile 1.90 g (11.0 mmol) was dissolved in tetrahydrofuran (70 mL) under a nitrogen atmosphere. Borane-methyl sulfide complex (10.0-10.2 M in tetrahydrofuran, 1.20 mL, 12.1 mmol) was added to the solution and the mixture heated to reflux for 3 hours. The solution was cooled to ambient temperature and a saturated solution of hydrochloric acid in methanol added slowly until a white precipitate formed. The solvent was removed in vacuo and the resulting white solid triturated (×4) with diethyl ether. Drying under vacuo gave 1.76 g (73%) of the title compound.

Workup

  1. customIn a 100 mL flask, fitted with a condenser
  2. temperaturethe mixture heated
  3. temperatureto reflux for 3 hours
  4. customformed
  5. customThe solvent was removed in vacuo
  6. customthe resulting white solid triturated (×4) with diethyl ether
  7. customDrying under vacuo

Sources & evidence

ORD record
ord-8d00eb7b06f44e52bc0f5aeb470d0040
Source dataset
uspto-grants-2003_09
Patent number
US06617351B1

Reaction notes

Loading…