Sodium Carbonate → Methyl 4-methyl-1-(5-nitropyridin-2-yl)piperidine-4-carboxylate

HRID 1713902Notes

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-chloro-5-nitropyridine (2.0 g, 12.62 mmol) in DMSO (20 mL) was added sodium carbonate (6.70 g, 63.08 mmol) followed by methyl 4-methylpiperidine-4-carboxylate hydrochloride (2.44 g, 12.62 mmol). The reaction mixture was heated to 60° C. for 2 hours. The reaction mixture was poured onto water (100 mL) and the suspension filtered, washed with water (4×150 mL) and dried to leave the title compound as a yellow solid (3.32 g, 11.89 mmol, 94%); 1H NMR (CDCl3) δ 1.26 (s, 3H), 1.46-1.52 (m, 2H), 2.21-2.25 (m, 2H), 3.26-3.32 (m, 2H), 3.74 (s, 3H), 4.16-4.20 (m, 2H), 6.56 (d, 1H), 8.18 (d, 1H), 9.03 (s, 1H); MS m/e MH+ 280.

Workup

additionThe reaction mixture was poured onto water (100 mL)
filtrationthe suspension filtered
washwashed with water (4×150 mL)
customdried

Sources & evidence

ORD record: ord-1fed2745c97c453385dc37047f9c8607
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795283B2

Reaction notes

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