Piperidine → (RS) methyl 3-{6-[2-(3-hydroxy-4-nitrophenyl)-acetylamino]-pyridin-3-yl}-butanoate

HRID 49711Notes

Reaction equation

HRID 49711 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH2:14][C:15]([NH:17][C:18]2[N:23]=[CH:22][C:21]([CH:24]([CH3:30])[CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:20][CH:19]=2)=[O:16])[CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])(=O)C.N1CCCCC1>ClCCl>[OH:4][C:5]1[CH:6]=[C:7]([CH2:14][C:15]([NH:17][C:18]2[N:23]=[CH:22][C:21]([CH:24]([CH3:30])[CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:20][CH:19]=2)=[O:16])[CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 17946633(RS) Methyl 3-{6-[2-(3-acetoxy-4-nitrophenyl)-acetylamino]-pyridin-3-yl}-butanoate

Product 1

HCID 17946660(RS) methyl 3-{6-[2-(3-hydroxy-4-nitrophenyl)-acetylamino]-pyridin-3-yl}-butanoateYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (RS) Methyl 3-{6-[2-(3-acetoxy-4-nitrophenyl)-acetylamino]-pyridin-3-yl}-butanoate (1.5 g, Reference Example 16) in dichloromethane (50 mL) was treated with a piperidine (5.0 mL). After stirring at room temperature for 1.5 hours the reaction mixture was washed with aqueous acetic acid (1M), then and dried over magnesium sulphate and then evaporated. The residual light brown oil was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:1, v/v) to give the title compound (1.26 g) as a pale yellow solid.

Workup

  1. washwas washed with aqueous acetic acid (1M)
  2. dry with materialdried over magnesium sulphate
  3. customevaporated
  4. additionThe residual light brown oil was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:1

Sources & evidence

ORD record
ord-304f44f285b847a68fd7d353097df1b4
Source dataset
uspto-grants-2004_03
Patent number
US06706738B2

Reaction notes

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