Sodium Carbonate → HCID 68507506, compound

HRID 1711328Notes

Reaction equation

HRID 1711328 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[CH3:17][C:18]1([CH3:24])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>C1(C)C=CC=CC=1>[CH3:17][C:18]1([CH3:24])[CH2:23][CH2:22][N:21]([C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 1381004,4-Dimethylpiperidine

Product 1

HCID 68507506HCID 68507506, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-chloro-3-nitropyridine (4.74 g, 0.03 mol) in toluene (50 mL), Na2CO3 (3.39 g, 32.0 mmol) and 4,4-dimethylpiperidine (J. Org. Chem., 47(20), 3890, (1982), 3.3 g, 0.033 mmol) were added. The resulting mixture was stirred at 50° C. for 1 h and concentrated in vacuo. Water (20 mL) and EtOAc (50 mL) were then added. The organic layer was separated, dried and concentrated to afford 4,4-dimethyl-3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl which was directly subjected to catalytic hydrogenation as described in Example 47, step (a) to obtain 4,4-dimethyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-3′-ylamine (4.1 g, 67%). Mass spectrum (ESI, m/z): Calcd. for C12H19N3, 206.1 (M+H), found 206.2.

Workup

  1. concentrationconcentrated in vacuo
  2. additionWater (20 mL) and EtOAc (50 mL) were then added
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-39ed86cfec1749208989861c5bf620d8
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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