Hydrochloric Acid → HCID 59322432, compound

HRID 1685152Notes

Reaction equation

HRID 1685152 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:14]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:17].Cl>C1C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:14][Br:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24614Phosphorus tribromideHCID 7173928HCID 7173928, compound

Product 1

HCID 59322432HCID 59322432, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
70 °C

Procedure

Charge (R)-(1-benzylpiperidin-2-yl)methanol (30.0 g, 0.146 mol, ˜1.0 eq., crude) in 350 mL benzene and add a solution of phosphorus tribromide (20.6 mL, 0.219 mol, 1.5 eq) in benzene at 0° C. under nitrogen atmosphere. Heat the reaction mass at 70° C. for 16 h. After completion of reaction, quench the reaction with saturated solution of sodium carbonate (100 mL) and extract the compound in EA (3×100 mL). Wash the organic layer with brine and dry over anhydrous sodium sulfate. Concentrate under reduced pressure and dissolve the solid residue in diethyl ether. Filter the dissolved portion and add slowly HCl (1.2 eq, 2 N in diethyl ether) and stir for 30 minutes at RT. Filter the precipitated salt and wash with EA followed by hexane. Dry under high vacuum to get 13.2 g of (R)-1-benzyl-2-(bromomethyl)piperidine as hydrochloride salt. MS(ES): m/z=268, 270 (M+H).

Workup

  1. customAfter completion of reaction
  2. customquench
  3. customthe reaction with saturated solution of sodium carbonate (100 mL)
  4. extractionextract the compound in EA (3×100 mL)
  5. washWash the organic layer with brine
  6. dry with materialdry over anhydrous sodium sulfate
  7. concentrationConcentrate under reduced pressure
  8. dissolutiondissolve the solid residue in diethyl ether
  9. filtrationFilter the dissolved portion
  10. filtrationFilter the precipitated salt
  11. washwash with EA
  12. customDry under high vacuum

Sources & evidence

ORD record
ord-3bdbd54cd1a04abea730e78bcf6a0814
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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