Benzyl Bromide → HCID 68532581, compound

HRID 1172275Notes

Reaction equation

HRID 1172275 reaction equation
[ClH:1].[NH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[ClH:1].[CH2:19]([N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH2:4][CH2:3]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 211985473-(Piperidin-4-yl)propanoic acid--hydrogen chloride (1/1)

Product 1

HCID 68532581HCID 68532581, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of (piperidin-4-yl)ethylcarboxylate hydrochloride (8.6 g, 44.4 mmol) and K2CO3 (24.5 g, 0.17 mol) in acetone (200 ml) was added benzylbromide (9.11 g, 53.3 mmol) and heated to reflux for 12 h. The solvent was evaporated in vacuo and the residue added H2O (200 ml). The aqueous layer was extracted with Et2O (3×100 ml) and the organic extracts dried over Na2SO4, filtered and evaporated in vacuo. The residue was dissolved in acetone and HCl bubbled into the solution to give the hydrochloride precipitate. The precipitate was filtered, dried and recrystallized from acetone to give the expected product as a white solid (11.03 g, 87.6%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 12 h
  3. customThe solvent was evaporated in vacuo
  4. additionthe residue added H2O (200 ml)
  5. extractionThe aqueous layer was extracted with Et2O (3×100 ml)
  6. dry with materialthe organic extracts dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. dissolutionThe residue was dissolved in acetone
  10. customHCl bubbled into the solution

Sources & evidence

ORD record
ord-994eb27cb7044999b23d79a67bb2cc37
Source dataset
uspto-grants-2010_11
Patent number
US07834010B2

Reaction notes

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