Ammonium Hydroxide → 2-Amino-6-(piperidin-1-ylmethyl)pyridine

HRID 460177Notes

Reaction equation

HRID 460177 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[N:3]=1.[NH4+:15].[OH-]>O>[NH2:15][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[N:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 137845442-Bromo-6-piperidin-1-ylmethylpyridine

Product 1

HCID 187716712-Amino-6-(piperidin-1-ylmethyl)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 2-bromo-6-(piperidylmethyl)pyridine (5.21 g, 20 mmol) in IpOH (30 mL) in a sealed tube at RT, a catalytic amount of Cu (100 mg) and 28–30% NH4OH (35 mL) were added. The stirred suspension was heated to 95° C. for 40 h. After cooling to RT, the reaction mixture was diluted with H2O (100 mL) and extracted with EtOAc (4×80 mL). The organic layers were combined, then washed with H2O (50 mL) followed by brine (50 mL). The organic layer was separated, dried over Na2SO4, filtered and concentrated under reduced pressure to yield the title compound as a dark yellow oil. This was used as crude. MS m/z: 193 (M+H)+.

Workup

  1. temperatureAfter cooling to RT
  2. extractionextracted with EtOAc (4×80 mL)
  3. washwashed with H2O (50 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-acc06917dec44dd4b47cbd19ddf89510
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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