2-Chloro-5-nitropyridine → Methyl [1-(5-nitropyridin-2-yl)piperidin-4-yl]acetate

HRID 1713818Notes

Reaction equation

HRID 1713818 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.Cl.[NH:12]1[CH2:17][CH2:16][CH:15]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH2:14][CH2:13]1.C(N=P1(N(CC)CC)N(C)CCCN1C)(C)(C)C>CC(N(C)C)=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH2:14][CH2:13]2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 783082-Chloro-5-nitropyridineHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 18423605Methyl (piperidin-4-yl)acetate--hydrogen chloride (1/1)

Product 1

HCID 47357980Methyl [1-(5-nitropyridin-2-yl)piperidin-4-yl]acetateYield 26.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 2-Chloro-5-nitropyridine (1.59 g, 10 mmol) and methyl piperidin-4-ylacetate hydrochloride (1.8 g, 10 mmol) (prepared as described in Patent Application WO 2000029407) in DMA (50 mL) was treated with 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine (BEMP) (15 g of a 2.2 mmol/g loading on polystyrene support, 33 mmol). The resulting mixture was stirred for 2.5 h then filtered through diatomaceous earth. Volatile material was removed by evaporation to give the title compound (740 mg, 21%) as a solid; 1H NMR δ 1.08-1.28 (2H, m), 1.77 (2H, d), 1.99-2.12 (1H, m), 2.29 (2H, d), 3.07 (2H, t), 3.60 (3H, s), 4.51 (2H, d), 6.94 (1H, d), 8.13-8.25 (1H, m), 8.95 (d, 1H); MS m/e MH+ 280.

Workup

  1. filtrationthen filtered through diatomaceous earth
  2. customVolatile material was removed by evaporation

Sources & evidence

ORD record
ord-415740148a5a46769081aac6cc3f4df1
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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