Ethanol → 1-(5-Ethoxy-2-nitrophenyl)piperidine

HRID 32899

Reaction equation

HRID 32899 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7]=1.[CH3:17][CH2:18][O-:19].[Na+].CCO>CN(C=O)C.CCOC(C)=O>[CH2:18]([O:19][C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7]=1)[CH3:17]

Participants

6

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 30960791-(5-Chloro-2-nitrophenyl)piperidine

Product 1

HCID 693102081-(5-Ethoxy-2-nitrophenyl)piperidineYield 54%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1-(5-chloro-2-nitro-phenyl)-piperidine (197 mg, 0.810 mmol, as prepared in Example 3, step (a)) in 1.5 mL of DMF was added 4 mL of 0.5 M NaOEt in EtOH (1.94 mmol). The resultant solution was heated at 90° C. for 24 h. The reaction was diluted with EtOAc (50 mL) and washed with water (50 mL), dried (Na2SO4) and concentrated in vacuo. Purification by preparative tic (20% EtOAc-hexane) gave 110 mg (54%) of the title compound. Mass spectrum (ESI, m/z): Calcd. for C13H18N2O3, 251.1 (M+H), found 251.1.

Workup

  1. washwashed with water (50 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by preparative tic (20% EtOAc-hexane)

Sources & evidence

ORD record
ord-22a516f3373b4dd59593530386bc9e19
Source dataset
uspto-grants-2008_09
Patent number
US07427683B2

Linked notes

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