Hydrochloric Acid → 2-Nitro-6-(piperidin-2-ylmethoxy)benzonitrile hydrochloride

HRID 332978Notes

Reaction equation

HRID 332978 reaction equation
[C:1]([C:3]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1C(OC(C)(C)C)=O)#[N:2].[ClH:27]>CCO>[ClH:27].[N+:24]([C:23]1[CH:22]=[CH:21][CH:20]=[C:4]([O:5][CH2:6][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][NH:8]2)[C:3]=1[C:1]#[N:2])([O-:26])=[O:25]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86714300HCID 86714300, compound

Product 1

HCID 867142982-Nitro-6-(piperidin-2-ylmethoxy)benzonitrile hydrochlorideYield 116%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of tert-butyl 2-((2-cyano-3-nitrophenoxy)methyl)piperidine-1-carboxylate (Example 26e, 1.02 g, 2.83 mmol) in EtOH (20 mL) was added HCl 1.25N in EtOH (11.3 mL, 14.13 mmol) and the reaction mixture was stirred at 80° C. under nitrogen for 1 hour. After cooling to room temperature, the reaction mixture was concentrated in vacuum. The oily residue was washed with Hexane:DCM (1:4) and the solvent concentrated in vacuum to give 2-nitro-6-(piperidin-2-ylmethoxy)benzonitrile hydrochloride (0.982 g, 116%). MS 262 (MH+).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated in vacuum
  3. washThe oily residue was washed with Hexane:DCM (1:4)
  4. concentrationthe solvent concentrated in vacuum

Sources & evidence

ORD record
ord-bc21f6c31eb245b28ba2b470b50ac790
Source dataset
uspto-grants-2014_11
Patent number
US08877922B2

Reaction notes

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