Tin dichloride dihydrate → tert-Butyl 4-(5-aminopyridin-2-ylamino)piperidine-1-carboxylate

HRID 1993670Notes

Reaction equation

HRID 1993670 reaction equation
Cl[Sn]Cl.O.[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][N:20]=2)[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]>C(OCC)(=O)C>[C:5]([O:9][C:10]([N:12]1[CH2:13][CH2:14][CH:15]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][N:20]=2)[CH2:16][CH2:17]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

4

Reactant 2

HCID 43835034Tin dichloride dihydrateHCID 53255493tert-Butyl 4-(5-nitropyridine-2-ylamino)piperidine-1-carboxylate

Product 1

HCID 53255724tert-Butyl 4-(5-aminopyridin-2-ylamino)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Add SnCl2.H2O (11.8 mmol, 2.7 g) over a solution of 4-(5-nitro-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (2.4 mmol, 0.8 g) in 20 mL of ethyl acetate. Stir the solution at room temperature overnight. Add aqueous NaHCO3 solution until the solution pH is basic and extract with ethyl acetate. Filter the suspension through a pad of Celite®. Combine the organic layers and wash with saturated aq. sodium chloride, dry over sodium sulfate, filter, and concentrate under reduced pressure to give the title compound. MS(ES): m/z=293 [M+H].

Workup

  1. extractionAdd aqueous NaHCO3 solution until the solution pH is basic and extract with ethyl acetate
  2. filtrationFilter the suspension through a pad of Celite®
  3. washCombine the organic layers and wash with saturated aq. sodium chloride
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-7c42cfc3400e47d0bc0571655a27dd4c
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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