HCID 66593552, compound → HCID 66593259, compound

HRID 1091658Notes

Reaction equation

HRID 1091658 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][N:12]2[CH3:17])=[O:10])=[CH:4][C:3]=1[N+:18]([O-])=O>C(O)C.[Pd]>[NH2:18][C:3]1[CH:4]=[C:5]([NH:8][C:9]([C@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][N:12]2[CH3:17])=[O:10])[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

4

Reactant 1

HCID 66593552HCID 66593552, compound

Product 1

HCID 66593259HCID 66593259, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (R)—N-(4-amino-3-nitrophenyl)-1-methylpiperidine-2-carboxamide (2.17 g, 7.8 mmol) in ethanol (75 mL) was degassed under vacuum and then backfilled with argon. 10% Palladium on carbon (0.44 g) was added and the mixture again degassed under vacuum. Hydrogen was introduced by a balloon and the reaction stirred at room temperature for 23 hr. The mixture was degassed by bubbling argon through it, and was then filtered through a pad of diatomaceous earth. The filtrate was concentrated to give (R)—N-(3,4-diaminophenyl)-1-methylpiperidine-2-carboxamide as a purple solid (1.78 g).

Workup

  1. customthe mixture again degassed under vacuum
  2. additionHydrogen was introduced by a balloon
  3. customThe mixture was degassed
  4. customby bubbling argon through it
  5. filtrationwas then filtered through a pad of diatomaceous earth
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-bce5d5b837d144189fabd3952f659b67
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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