HCID 57757112, compound → β-Cyclohexylbenzeneethanamine

HRID 902613Notes

Reaction equation

HRID 902613 reaction equation
[N:1]([CH2:4][CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[N+]=[N-]>CO.[Pd]>[CH:12]1([CH:5]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:4][NH2:1])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 1

HCID 57757112HCID 57757112, compound

Product 1

HCID 434345β-CyclohexylbenzeneethanamineYield 104.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirring solution of (2-azido-1-cyclohexyl-ethyl)-benzene (700 mg, 3.06 mmol) in methanol (20 mL) was added palladium on carbon (70 mg, 10 wt. %). The mixture was stirred at 50 Psi H2 overnight, filtered, and washed with methanol, and the filtrate was concentrated in vacuo to give 650 mg (99% yield) of title compound as an oil. 1 H-NMR (400 MHz, CDCl3) δ 7.34-7.16 (m, 5H), 3.13 (t, 1H, J=4.5 Hz), 2.92 (t, 1H, J=2.3 Hz), 2.40 (m, 1H), 1.73-0.74 (m, 11H).

Workup

  1. filtrationfiltered
  2. washwashed with methanol
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b12f4583eaa74ad692f18a893d96ac5d
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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