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Ammonium Chloride → Benzyl [(3S)-1-(3-amino-5-cyanopyridin-4-yl)piperidin-3-yl]carbamate

HRID 924439
Notes
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Reaction equation

HRID 924439 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[C:7]([N+:26]([O-])=O)[C:8]=1[N:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:10]1)#[N:2].[Cl-].[NH4+]>CCO.O.[Fe]>[NH2:26][C:7]1[CH:6]=[N:5][CH:4]=[C:3]([C:1]#[N:2])[C:8]=1[N:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:10]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86726889Benzyl [(3S)-1-(3-cyano-5-nitropyridin-4-yl)piperidin-3-yl]carbamate

Product 1

HCID 86726890Benzyl [(3S)-1-(3-amino-5-cyanopyridin-4-yl)piperidin-3-yl]carbamateYield 92.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolvent
HCID 962
Water
Solvent

Conditions

Temperature
85 °C

Procedure

A mixture of benzyl [(3S)-1-(3-cyano-5-nitropyridin-4-yl)piperidin-3-yl]carbamate (0.065 g, 0.17 mmol), iron (0.084 g, 1.5 mmol), and ammonium chloride (0.091 g, 1.7 mmol) in EtOH (2 mL) and water (0.2 mL) was stirred at 85° C. for 15 min. The crude reaction mixture was filtered through a pad of diatomaceous earth and the inorganics were washed thoroughly with EtOH. The filtrate was concentrated under reduced pressure and the residue was partitioned between water and EtOAc. The organic fraction was washed with water, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford the sub-title compound (0.055 g). LCMS (ESI) calc. for C19H22N5O2 m/z=352.2 [M+H]+. found 352.1.

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered through a pad of diatomaceous earth
  3. washthe inorganics were washed thoroughly with EtOH
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was partitioned between water and EtOAc
  6. washThe organic fraction was washed with water, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3dfba6df65cb4832a51ef3b8c1594ce4
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09278950B2

Reaction notes

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