Methanol → β,β-Dimethylbenzenepropanamine

HRID 566706Notes

Reaction equation

HRID 566706 reaction equation
[CH3:1][C:2]([CH3:14])([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][N:4]=[N+]=[N-].CO.[H][H]>[Pd].O1CCCC1>[C:8]1([CH2:7][C:2]([CH3:14])([CH3:1])[CH2:3][NH2:4])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 22346614HCID 22346614, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13707364β,β-Dimethylbenzenepropanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,2-dimethyl-3-phenyl-1-azidopropane (3 gm), 10% Pd-C, methanol (60 mL) and tetrahydrofuran (15 mL) was stirred under 1 atmosphere of hydrogen at rt for 18 h. The mixture was filtered and concentrated to give the title compound as an oil, MS (m/z): 164.1 (M+H)+; C11H17N requir. 163.1.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7c7c37ab25c94c708f6b761904902be5
Source dataset
uspto-grants-2001_01
Patent number
US06174901B1

Reaction notes

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