Hexane → Ethyl 1-(5-bromo-3-pyridyl)-4-methyl-piperidine-4-carboxylate

HRID 712203Notes

Reaction equation

HRID 712203 reaction equation
Cl.[CH3:2][C:3]1([C:9]([OH:11])=[O:10])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C([O-])([O-])=O.[Cs+].[Cs+].Br[C:19]1[CH:20]=[N:21][CH:22]=[C:23]([Br:25])[CH:24]=1.[CH3:26][CH2:27]CCCC>CS(C)=O>[Br:25][C:23]1[CH:24]=[C:19]([N:6]2[CH2:7][CH2:8][C:3]([CH3:2])([C:9]([O:11][CH2:26][CH3:27])=[O:10])[CH2:4][CH2:5]2)[CH:20]=[N:21][CH:22]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 10796Cesium carbonateHCID 693693,5-DibromopyridineHCID 510003794-Methylpiperidine-4-carboxylic acid hydrochloride

Product 1

HCID 66977152Ethyl 1-(5-bromo-3-pyridyl)-4-methyl-piperidine-4-carboxylateYield 14%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-methylpiperidine-4-carboxylate hydrochloride (3.6 g, 21.10 mmol) in DMSO (5 mL) was added Cs2CO3 (1.63 g, 5 mmol) at rt. The resulting mixture was stirred at rt for 10 min followed by addition of 3,5-dibromopyridine (1.0 g, 4.20 mmol). The reaction was heated up to 150° C. for 48 h. After completion (by TLC), the reaction mixture was poured into 100 mL of ice-cold water and extracted with EtOAc (3×100 mL). The combined organics were washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel by using 20.0% EtOAc:hexane to obtain a viscous liquid product (0.2 g, 14% yield). MS: 327.08 [M+H]+.

Workup

  1. temperatureThe reaction was heated up to 150° C. for 48 h
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude residue was purified over 100-200 M silica-gel

Sources & evidence

ORD record
ord-8a8e40439d944a59bf726a063be720fb
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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