Sodium Carbonate → HCID 58869858, compound

HRID 2382161Notes

Reaction equation

HRID 2382161 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:5])[CH3:2].Cl[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=1.C([O-])([O-])=O.[Na+].[Na+]>CS(C)=O>[CH2:1]([O:3][C:4](=[O:5])[CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=2)[CH2:9][CH2:8]1)[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 2760465Ethyl 2-(piperidin-4-yl)acetate

Product 1

HCID 58869858HCID 58869858, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-(ethoxycarbonylmethyl)piperidine (0.0222 mol) and 2-chloro-5-nitropyridine (0.0222 mol) in DMSO (40 ml) was stirred in the presence of Na2CO3 during 2 hours. The reaction mixture was cooled to room temperature and poured into an ice/water mixture. The resulting precipitate was filtered and washed with water. The reaction product was purified by recrystallisation from a mixture of ethyl acetate and hexane, yielding (5′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-acetic acid ethyl ester (intermediate 1, mp. 99-101° C.).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water
  3. customThe reaction product was purified by recrystallisation from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-34d992fcbcf2465783467fbf2c6fa6b5
Source dataset
uspto-grants-2012_09
Patent number
US08258304B2

Reaction notes

Loading…