1-Benzyl-N-(2-nitrocyclohexyl)piperidin-4-amine → N~1~-(1-Benzylpiperidin-4-yl)cyclohexane-1,2-diamine

HRID 647825Notes

Reaction equation

HRID 647825 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]2[N+:21]([O-])=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.[Ni]>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]2[NH2:21])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 132117921-Benzyl-N-(2-nitrocyclohexyl)piperidin-4-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 13211793N~1~-(1-Benzylpiperidin-4-yl)cyclohexane-1,2-diamineYield 98.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

In this reference example, 1.0 g of 1-benzyl-4-(2-nitro-cyclohexylamino)-piperidine obtained in Reference Example 16 is dissolved in 25 ml of ethanol. Then, 1.0 g of a Raney-nickel catalyst is added thereto and the mixture is stirred at room temperature in the atmosphere of hydrogen under the atmospheric pressure. The stirring is ceased when the solution has absorbed the theoretical amount of hydrogen, and the reaction solution is filtered. The filtrate is concentrated. Consequently, 0.89 g of 1-benzyl-4-(2-aminocyclohexylamino)-piperidine is obtained as the residue.

Workup

  1. customhas absorbed the theoretical amount of hydrogen
  2. filtrationthe reaction solution is filtered
  3. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-70b95b8969a24b6c873cfaa91cd43e27
Source dataset
uspto-grants-1983_10
Patent number
US04410528

Reaction notes

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