Sodium Cyanide → Dimethyl-(4-nitro-3-piperidin-1-yl-phenyl)-amine

HRID 32894

Reaction equation

HRID 32894 reaction equation
F[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.[C-]#N.[Na+].CCO.[CH3:23][N:24](C=O)[CH3:25]>CCOC(C)=O>[CH3:23][N:24]([CH3:25])[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

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 19794673N,N-dimethylformamide ethanolHCID 532567081-(5-Fluoro-2-nitrophenyl)piperidine

Product 1

HCID 69312829Dimethyl-(4-nitro-3-piperidin-1-yl-phenyl)-amineYield 27%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 1-(5-fluoro-2-nitro-phenyl)-piperidine (294 mg, 1.31 mmol, as prepared in the previous step) in 8 mL EtOH-DMF (v/v) was added NaCN (128 mg, 2.6 mmol). The reaction was heated to 130° C. in a sealed tube for 24 h. The reaction was diluted with EtOAc (50 mL) and washed with water (2×50 mL). Chromatography (50% EtOAc-hexane) of the crude product afforded 88 mg (27%) the title compound as well as 78 mg (24%) (1-(5-ethoxy-2-nitro-phenyl)-piperidine as yellow solids. Mass spectrum (ESI, m/z): Calcd. for C13H19N3O2, 250.1 (M+H), found 250.0.

Workup

  1. washwashed with water (2×50 mL)

Sources & evidence

ORD record
ord-86b810c8a16945c2aa27b3ff2b97ca07
Source dataset
uspto-grants-2008_09
Patent number
US07427683B2

Linked notes

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