Hydrochloric Acid → HCID 13925231, compound

HRID 501213Notes

Reaction equation

HRID 501213 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[CH2:15][CH:14]=[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.B(F)(F)F.CC[O:30]CC.[OH-].[Na+].OO.Cl>COCCOCCOC.O>[CH2:3]([N:10]1[CH2:11][CH2:12][CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])[CH:14]([OH:30])[CH2:15]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 10707808HCID 10707808, compound

Product 1

HCID 13925231HCID 13925231, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8150DiglymeSolvent2×

Procedure

Sodium borohydride (0.590 g, 15.94 mmol) was added at once to a solution of 1-benzyl-4-(2-methoxyphenyl)-1,2,3,6-tetrahydropyridine (2.0 g, 7.16 mmol) in (7 mL) anhydrous diglyme at 0° C. The reaction mixture was warmed to room temperature and a solution of borontrifluoride etherate (2.0 g 14.2 mmol) in (2 mL) diglyme was added dropwise under a N2. The reaction mixture was stirred at room temperature for 2 h. Water (0.8 mL) was then added to the reaction mixture slowly followed by 6N NaOH (1.8 mL). The reaction mixture was heated to 50° C. for another 45 min. and then 30% H2O2 (1.7 mL, 14.7 mmol) was added. The reaction mixture was stirred for another 45 min., Concentrated HCl (1.7 mL) was added and the solvents were evaporated in vacuum. Water (7 mL) was added to the residue and the solvent again evaporation. The residue was quenched with saturated ammonium hydroxide solution and extracted with DCM (2×50 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give 1-benzyl-4-(2-methoxyphenyl)piperidin-3-ol (1.0 g, 50%); 1H NMR (200 MHz, CDCl3): δ 1.79-2.18 (m, 5H), 2.91-3.045 (m, 2H), 3.184-3.256 (dd, J=10.4, 4.0 Hz, 2H), 3.615 (s, 2H), 3.827 (s, 3H), 3.785-3.949 (m, 1H), 6.892 (d, J=8.5 Hz, 2H), 6.974 (t, J=7.5 Hz, 1H), 7.188-7.416 (m, 7H); m/e=297 (M+1).

Workup

  1. temperatureThe reaction mixture was heated to 50° C. for another 45 min.
  2. stirringThe reaction mixture was stirred for another 45 min.
  3. customthe solvents were evaporated in vacuum
  4. additionWater (7 mL) was added to the residue
  5. customthe solvent again evaporation
  6. customThe residue was quenched with saturated ammonium hydroxide solution
  7. extractionextracted with DCM (2×50 mL)
  8. dry with materialThe organic layer was dried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7a3285b7de9846d3a65e0e6bfa1f4f35
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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