Triethylamine → 4-Benzyl-5-bromo-2-(4-hydroxypiperidino)pyridine

HRID 1359394Notes

Reaction equation

HRID 1359394 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([Br:20])=[CH:9][N:8]=1)(=O)=O.Cl.[OH:24][CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(N(CC)CC)C>CN(C)C=O>[CH2:13]([C:11]1[C:10]([Br:20])=[CH:9][N:8]=[C:7]([N:28]2[CH2:29][CH2:30][CH:25]([OH:24])[CH2:26][CH2:27]2)[CH:12]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 162124994-Hydroxypiperidinium chlorideHCID 181821814-Benzyl-5-bromo-2-pyridyl trifluoromethanesulfonate

Product 1

HCID 181823874-Benzyl-5-bromo-2-(4-hydroxypiperidino)pyridineYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 550 mg of 4-benzyl-5-bromo-2-pyridyl trifluoromethanesulfonate (Production Example 1), 600 mg of 4-hydroxypiperidine hydrochloride, 1 ml of triethylamine and 2 ml of N,N-dimethylformamide was heated under stirring for 3 hours in an oil bath kept at 100° C. in a nitrogen atmosphere. After cooling as it was, the reaction mixture was extracted with ethyl acetate/water. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was subjected to silica gel column chromatography and eluted with 50% ethyl acetate/hexane, to give 270 mg of the target compound.

Workup

  1. temperaturewas heated
  2. customkept at 100° C. in a nitrogen atmosphere
  3. temperatureAfter cooling as it
  4. extractionthe reaction mixture was extracted with ethyl acetate/water
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. washeluted with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-033c4dbfa38c4b598562776b157171f4
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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