HCID 68509534, compound → 1,1-Dimethylethyl 4-[(2-amino-4-methylphenyl)amino]-1-piperidinecarboxylate

HRID 1716560Notes

Reaction equation

HRID 1716560 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[N+:22]([O-])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[NH2:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 68509534HCID 68509534, compound

Product 1

HCID 588522881,1-Dimethylethyl 4-[(2-amino-4-methylphenyl)amino]-1-piperidinecarboxylateYield 90.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-(4-methyl-2-nitro-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (9.5 g, 28.4 mmol) in ethanol (150 mL) was added 10% Pd/C (125 mg) and the reaction mixture was shaken under H2 (50 psi) at rt for 1 h. The catalyst was then removed by filtration through a pad of Celite® and washed with ethanol. The filtrate was concentrated in vacuo to provide 4-(2-amino-4-methyl-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (7.83 g) in 90% yield.

Workup

  1. customThe catalyst was then removed by filtration through a pad of Celite®
  2. washwashed with ethanol
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fc9efd3eb23a46cfb00f0a537f66af38
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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