Hydrochloric Acid → HCID 131730080, compound

HRID 2189054Notes

Reaction equation

HRID 2189054 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.[OH-].[Na+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:18]([O:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 131730081HCID 131730081, compound

Product 1

HCID 131730080HCID 131730080, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Dissolve 15 g (74.5 mmol) of tert-butyl(+/−)-3-hydroxypiperidinecarbamate while heating in 86.5 ml of toluene and successively add 11.9 ml of 50% sodium hydroxide solution (447 mmol), 2.53 g (7.5 mmol) of tetra-n-butylammonium hydrogen sulphate and 11.5 ml (96.9 mmol) of benzyl bromide. Stir the biphasic reaction mixture vigorously at 70° C. for 4 h. After cooling, add water and neutralize with conc. hydrochloric acid. Remove the organic phase, dry it over sodium sulphate and concentrate it under reduced pressure. Purify the crude product by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 30:1→10:1). 16.21 g of the target product are obtained (74.6% of theory).

Workup

  1. customthe biphasic reaction mixture vigorously at 70° C. for 4 h
  2. temperatureAfter cooling
  3. customRemove the organic phase
  4. dry with materialdry it over sodium sulphate
  5. concentrationconcentrate it under reduced pressure
  6. customPurify the crude product by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 30:1→10:1)

Sources & evidence

ORD record
ord-e2486da114e841968140c552745afd0e
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

Loading…