Acetic Acid → 2-Bromo-6-piperidin-1-ylmethylpyridine

HRID 1097244Notes

Reaction equation

HRID 1097244 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=O)[CH:5]=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH2:8][N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[N:7]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8082PiperidineHCID 516892Sodium BicarbonateHCID 27570096-Bromopyridine-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 137845442-Bromo-6-piperidin-1-ylmethylpyridineYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 6-bromopyridine-2-carbaldehyde (25 g, 135 mmol) in dichloromethane (500 ml) was slowly added piperidine (12.6 g, 149 mmol) at 10° C. After stirring for 15 minutes at 10° C., acetic acid (8.9 g, 149 mmol) was added, followed by the portionwise addition of sodium triacetoxyborohydride, while the temperature was kept at 5-10° C. After stirring for 2 h at room temperature the reaction mixture was poured into a saturated aqueous solution of sodium hydrogen carbonate. The product was extracted into dichloromethane and the combined organic phases were washed with brine, dried over sodium sulphate and concentrated under reduced pressure. Column chromatography afforded 2-bromo-6-(piperidin-1-ylmethyl)pyridine (30 g) as a colourless oil.

Workup

  1. customat 10° C
  2. customwas kept at 5-10° C
  3. stirringAfter stirring for 2 h at room temperature the reaction mixture
  4. extractionThe product was extracted into dichloromethane
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5a6bcd1685844117ae293904b94b0d1f
Source dataset
uspto-grants-2012_03
Patent number
US08143246B2

Reaction notes

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