Water → HCID 59464298, compound

HRID 1713917Notes

Reaction equation

HRID 1713917 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:17][C:18]1([CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.O>CS(C)=O>[CH3:17][C:18]1([CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH2:23][CH2:22][N:21]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 59090877HCID 59090877, compound

Product 1

HCID 59464298HCID 59464298, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-chloro-5-nitropyridine (2.97 g, 18.77 mmol) in DMSO (30 mL) was added sodium carbonate (6.4 g, 60.38 mmol) followed by methyl (4-methylpiperidin-4-yl)acetate (3.21 g, 18.77 mmol) (prepared according to the procedures described by Janet Ralbovsky, Joseph Lisko and Wei He, Synthetic Communications, 2005, 35 (12), 1613-1625 and Gerhard Hund, and Woldemar Schneider, Chem Ber 1980,113 (2), 401-7). The reaction mixture was heated to 60° C. for 1.5 hours, then allowed to cool and water (100 mL) was added. The suspension filtered, and dried to leave a yellow solid (3.70 g, 12.62 mmol, 67%). 1H NMR δ 1.08 (s, 3H), 1.45-1.48 (m, 2H), 1.55-1.61 (m, 2H), 2.38 (s, 2H), 3.59 (s, 3H), 3.64-3.70 (m, 2H), 3.85-3.91 (m, 2H), 6.95 (d, 1H), 8.19 (d, 1H), 8.95 (s, 1H); MS m/e MH+ 294.

Workup

  1. customprepared
  2. temperatureto cool
  3. filtrationThe suspension filtered
  4. customdried

Sources & evidence

ORD record
ord-e925d77bb93c4c92a09e6eae4aaeef3f
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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