Hydrochloric Acid → N2-(1-benzylpiperidin-4-yl)pyridine-2,3-diamine

HRID 1068168Notes

Reaction equation

HRID 1068168 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:20]([N+:21]([O-])=O)=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[Sn]Cl.Cl>C1COCC1.CCOC(C)=O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:20]([NH2:21])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 2823254N-(1-benzylpiperidin-4-yl)-3-nitropyridin-2-amine

Product 1

HCID 21192982N2-(1-benzylpiperidin-4-yl)pyridine-2,3-diamine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1-Benzyl-piperidin-4-yl)-(3-nitro-pyridin-2-yl)-amine (from Step A) in 10 mL of THF was added 2.4 g of SnCl2 and 1 mL of concentrated HCl at room temperature, stirred at room temperature for 2 hours. The reaction was diluted with 40 mL of EtOAc and washed with 30 mL of saturated NaHCO3 aqueous solution. After separating layers, the aqueous phase was extracted with 2×15 mL EtOAc. The combined organic phases were washed with 15 mL of brine, dried over MgSO4 and concentrated under reduced pressure to give 603 mg of yellow soid.

Workup

  1. washwashed with 30 mL of saturated NaHCO3 aqueous solution
  2. customAfter separating layers
  3. extractionthe aqueous phase was extracted with 2×15 mL EtOAc
  4. washThe combined organic phases were washed with 15 mL of brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customto give 603 mg of yellow soid

Sources & evidence

ORD record
ord-290f71f084b8469f867d3d61c5d8c8f1
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

Loading…