Hydrochloric Acid → 104178-90-7

HRID 2117606Notes

Reaction equation

HRID 2117606 reaction equation
[CH2:1]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[ClH:13]>CCO.[Pd]>[ClH:13].[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH2:10])=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 1407304-Butylbenzonitrile

Product 1

HCID 16090352104178-90-7Yield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-butylbenzonitrile (30.09 g) in EtOH (380 mL) and HCl (4N in dioxane, 50 mL, 200 mmol) was hydrogenated at 50 psi on a Parr shaker in the presence of 10% palladium on carbon (6.09 g). The catalyst was removed via filtration through Celite® and the solution was concentrated in vacuo. The residue was suspended in Et2O and filtered to provide 4-butylbenzylamine hydrochloride as an off-white solid (32.47 g). 1H NMR (400 MHz, CD3OD) δ 7.33 (d, 2H), 7.22 (d, 2H), 4.04 (s, 2H), 2.60 (t, 2H), 1.56 (m, 2H), 1.31 (m, 2H), 0.89 (t, 3H).

Workup

  1. customThe catalyst was removed via filtration through Celite®
  2. concentrationthe solution was concentrated in vacuo
  3. filtrationfiltered

Sources & evidence

ORD record
ord-033cda889f44488a8bd1cb63587c12e6
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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