Hydrochloric Acid → 3-Isopropylbenzylamine Hydrochloride

HRID 348874

Reaction equation

HRID 348874 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8])([CH3:3])=[CH2:2].[ClH:12]>C(O)C.C(O)(=O)C.CO.C(OCC)C.[Pd]>[ClH:12].[CH:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][NH2:8])([CH3:3])[CH3:2]

Participants

8

Reactant 2

HCID 313Hydrochloric AcidHCID 121802503-Isopropenylbenzonitrile

Product 1

HCID 210858343-Isopropylbenzylamine Hydrochloride

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 3-isopropenylbenzonitrile (6.0 g, 41.9 mmol) and 10% Pd/C (600 mg) in ethanol (65 mL) and acetic acid (2.4 mL) is degassed with nitrogen for 15 min, and shaken under an atmosphere of hydrogen at 50 psi for 12 h. The reaction mixture is filtered through diatomaceous earth and concentrated under reduced pressure to provide an oil. The oil is dissolved in methanol (5 mL) and hydrochloric acid (15 mL of a 1 M solution in diethyl ether) is added. The resulting precipitate is collected by filtration to provide the title compound. APCI MS m/z 149 [M+H]+.

Workup

  1. filtrationThe reaction mixture is filtered through diatomaceous earth
  2. concentrationconcentrated under reduced pressure
  3. customto provide an oil
  4. filtrationThe resulting precipitate is collected by filtration

Sources & evidence

ORD record
ord-9560c8dd9b2a40fa848fd7df53423eff
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

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