(2-Nitrophenyl)(tetrahydropyran-3-yl)amine → N-(Tetrahydropyran-3-yl)benzene-1,2-diamine

HRID 242830Notes

Reaction equation

HRID 242830 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][O:13][CH2:12]1)([O-])=O>CCOC(C)=O.[Pd]>[O:13]1[CH2:14][CH2:15][CH2:16][CH:11]([NH:10][C:5]2[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:12]1

Participants

4

Reactant 1

HCID 63363726(2-Nitrophenyl)(tetrahydropyran-3-yl)amine

Product 1

HCID 63360336N-(Tetrahydropyran-3-yl)benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2-nitrophenyl)(tetrahydropyran-3-yl)amine (0.72 g, 3.24 mmol) and 10% Pd/C (200 mg) in EtOAc (30 mL) was degassed with a stream of nitrogen and stirred at RT under a hydrogen atmosphere for 3 days. The suspension was then filtered through a pad of celite and the filtrate was concentrated in vacuo affording N-(Tetrahydropyran-3-yl)benzene-1,2-diamine as a colourless oil (quantitative). 1H NMR (CDCl3, 400 MHz): δ 6.80 (1H, t, J=7.55 Hz), 6.75-6.62 (3H, m), 4.00 (1H, d, J=11.24 Hz), 3.84-3.71 (1H, m), 3.67-3.16 (6H, m), 2.07-1.92 (1H, m), 1.87-1.73 (1H, m), 1.72-1.56 (2H, m).

Workup

  1. customwas degassed with a stream of nitrogen
  2. filtrationThe suspension was then filtered through a pad of celite
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-446ec392b7e64802b5a28ea0c8d2a5df
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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