HCID 43610331, compound → HCID 43609747, compound

HRID 242825Notes

Reaction equation

HRID 242825 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][O:14][CH2:13][CH2:12]1)([O-])=O>CCOC(C)=O.[Pd]>[O:14]1[CH2:13][CH2:12][CH:11]([NH:10][C:5]2[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:16][CH2:15]1

Participants

4

Reactant 1

HCID 43610331HCID 43610331, compound

Product 1

HCID 43609747HCID 43609747, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2-nitrophenyl)(tetrahydropyran-4-yl)amine (1.58 g, 7.09 mmol) and 10% Pd/C (400 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-4-yl)benzene-1,2-diamine as a colourless oil (quantitative). 1H NMR (CDCl3, 400 MHz): δ 6.83-6.64 (4H, m), 4.01 (2H, d, J=11.69 Hz), 3.57-3.41 (3H, m), 3.40-3.19 (3H, bs), 2.08-1.99 (2H, m), 1.59-1.46 (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-66e19af1c1814dfcb22dbbb8a629899c
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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