Imidazole → 1-[4-(2-Bromo-ethyl)-piperidin-1-yl]-ethanone

HRID 445078Notes

Reaction equation

HRID 445078 reaction equation
O[CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10](=[O:12])[CH3:11])[CH2:6][CH2:5]1.C(Br)(Br)(Br)[Br:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1>ClCCl>[Br:14][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10](=[O:12])[CH3:11])[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 21468226Ethanone,1-[4-(2-hydroxyethyl)-1-piperidinyl]-

Product 1

HCID 578501381-[4-(2-Bromo-ethyl)-piperidin-1-yl]-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-[4-(2-hydroxy-ethyl)-piperidin-1-yl]-ethanone (0.500 g, 2.92 mmol) in dichloromethane (15 mL) was added carbon tetrabromide 1.45 g, 4.38 mmol), triphenyl phosphine (0.728 g, 2.77 mmol) and imidazole (0.398 g, 5.84 mmol) at 0° C. The temperature of the reaction mixture was slowly raised to room temperature and stirring continued at rt for 18 h. The reaction was diluted with dichloromethane and washed with water. The organic layer was dried (Na2SO4), filtered, and the solvent was evaporated. The product was chromatographed over silica gel using gradient of 0-10% methanol in dichloromethane. GC-MS m/z 235.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe product was chromatographed over silica gel using gradient of 0-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-784f09f46cb34b3fba6e2c542fd07f55
Source dataset
uspto-grants-2013_07
Patent number
US08476285B2

Reaction notes

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