Benzyl Bromide → HCID 11322245, compound

HRID 2167090Notes

Reaction equation

HRID 2167090 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][CH2:9][CH2:10][OH:11].C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[CH2:18]([N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][CH2:9][CH2:10][OH:11])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 201565333-(2-Piperidyl)-1-propanol Hydrochloride

Product 1

HCID 11322245HCID 11322245, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of compound 21 (3 g, 16.71 mmol) in ethanol (23 mL) was added K2CO3 (11.5 g, 83.55 mmol) portion-wise at ice cold conditions. Benzyl bromide (2 mL, 16.71 mmol) was then added and the reaction mixture was heated at reflux for 2 hours. The reaction mixture was filtered, and washed with EtOAc. The filtrate was concentrated, the residue was dissolved in EtOAc, washed with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered and concentrated. The crude material was purified by 230-400 silica gel column chromatography using 1-3% MeOH-DCM as eluent to yield compound 22.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe reaction mixture was filtered
  4. washwashed with EtOAc
  5. concentrationThe filtrate was concentrated
  6. dissolutionthe residue was dissolved in EtOAc
  7. washwashed with saturated NaHCO3 solution and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude material was purified by 230-400 silica gel column chromatography

Sources & evidence

ORD record
ord-6bbbb82dd6a94262800a3df520775fdb
Source dataset
uspto-grants-2015_06
Patent number
US09044482B2

Reaction notes

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