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

HRID 1716592Notes

Reaction equation

HRID 1716592 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]>C1COCC1.CO.[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

5

Reactant 1

HCID 68509534HCID 68509534, compound

Product 1

HCID 588522881,1-Dimethylethyl 4-[(2-amino-4-methylphenyl)amino]-1-piperidinecarboxylateYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(4-methyl-2-nitrophenylamino)-piperidine-1-carboxylic acid tert-butyl ester (3.0 g, 8.96 mmol) was dissolved in a mixture of THF and CH3OH (100 mL). Then 10% of Pd on carbon (0.60 g) was added. The mixture was hydrogenated at 50 psi for 2 hrs. The mixture was filtered through a pad of Celite® and washed with CH3OH. The filtrate was evaporated to dryness to give a pink residue as 4-(2-amino-4-methylphenylamino)-piperidine-1-carboxylic acid tert-butyl ester (2.72 g, 100%).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite®
  2. washwashed with CH3OH
  3. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-9e70424835d54be5803b381626512cd1
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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