Potassium Hydroxide → HCID 12544573, compound

HRID 851787Notes

Reaction equation

HRID 851787 reaction equation
CO[C:3]1[CH:4]=[C:5]2[C@@:13]34[C@@H:17]5[CH2:18][C@H:19]6C(CN5CC3)=CCO[C@H]3CC(=O)N([C@H:12]4[C@@H:20]63)C2=[CH:7][C:8]=1[O:9]C.[OH-].[K+]>O>[C:13]1([CH2:5][CH2:4][CH2:3][C@@H:8]([OH:9])[CH3:7])[CH:17]=[CH:18][CH:19]=[CH:20][CH:12]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 442021Brucine

Product 1

HCID 12544573HCID 12544573, compoundYield 20.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

S-Brucine salt of the preceding Example (10.0 kg., 14.2 moles) was combined with 121 liters of toluene and 143.8 liters of water. With stirring the pH was adjusted to 1.7 by addition of about 6 liters of 3N HCl. The aqueous layer was separated and extracted with 2×37.85 liters of toluene. Brucine was precipitated from the aqueous layer by adjusting the pH to 11.5 with 50% NaOH. Recrystallization from isopropyl alcohol provides brucine suitable for reuse. The toluene layers were combined, back-washed with 75 liters of water, concentrated to 45 liters. Fresh water (65 liters) and then KOH (85%, 1.90 kg., 28.8 moles) were added and the mixture stirred for one hour at room temperature and then 2 hours at 82°-84° C. The reaction mixture was cooled to 25° C., the toluene layer separated and the aqueous layer washed 3×19 liters of toluene. The toluene layers were combined, washed 1×20 liters saturated NaCl, dried (MgSO4), filtered and concentrated to yield title product as an oil (1.91 kg.), purified by distillation in vacuo (1.64 kg., b.p. 85°-92°/0.1 mm., [alpha]D25 +8.24 to +8.57°). Yield=20.4%.

Workup

  1. washback-washed with 75 liters of water
  2. concentrationconcentrated to 45 liters
  3. custom2 hours
  4. customat 82°-84° C
  5. temperatureThe reaction mixture was cooled to 25° C.
  6. customthe toluene layer separated
  7. washthe aqueous layer washed 3×19 liters of toluene
  8. washwashed 1×20 liters saturated NaCl
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-a0a60f10499c482bb59f64282b51a38a
Source dataset
uspto-grants-1983_05
Patent number
US04386205

Reaction notes

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