Ethanol → HCID 59794650, compound

HRID 32916Notes

Reaction equation

HRID 32916 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([CH3:14])[CH2:10][CH2:9]2)[CH:7]=1.[Cl-].[NH4+].CCO>[Fe].O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:15])=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([CH3:14])[CH2:10][CH2:9]2)[CH:7]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 59794652HCID 59794652, compound

Product 1

HCID 59794650HCID 59794650, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A flask charged with 1-(5-bromo-2-nitro-phenyl)-4-methyl-piperidine (1.0 g, 3.3 mmol) (as prepared in the previous step), ammonium chloride (1.8 g, 33 mmol), iron powder (0.93 g, 16 mmol), EtOH (12 mL) and water (6 mL) was heated at 80° C. for 1 h. The reaction was filtered though Celite, concentrated and eluted from a 20-g SPE cartridge (silica) with 100% DCM to give 0.80 g (91%) of the title compound as a yellow oil. Mass spectrum (ESI, m/z): Calcd. for C12H17BrN2, 269.1/271.1 (M+H), found 269.1/271.1.

Workup

  1. filtrationThe reaction was filtered though Celite
  2. concentrationconcentrated
  3. washeluted from a 20-g SPE cartridge (silica) with 100% DCM

Sources & evidence

ORD record
ord-5f7b03f41c1142fe912f4fc8431f8071
Source dataset
uspto-grants-2008_09
Patent number
US07427683B2

Reaction notes

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