Hydrochloric Acid → HCID 19814218, compound

HRID 466595Notes

Reaction equation

HRID 466595 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][C:12]([O:17][C:18](=[O:24])NCCCC)([C:15]#[CH:16])[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:25]1CCOCC1>>[CH2:2]([N:9]1[CH2:10][CH2:11][C:12]2([O:17][C:18](=[O:24])[O:25][C:15]2=[CH2:16])[CH2:13][CH2:14]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 19814307HCID 19814307, compound

Product 1

HCID 19814218HCID 19814218, compoundYield 80.6%

Procedure

Dry gaseous hydrogen chloride is introduced at 20° to 50° C. during 2.5 to 3 hours into a solution containing 31.4 g of 1-benzyl-4-butylcarbamoyloxy-4-ethynylpiperidine in 157 ml of anhydrous dioxane. After standing overnight the reaction mixture is evaporated in a water bath of 40° to 50° C. temperature under reduced pressure. After adding 200 ml of water to the evaporation residue the base is liberated by sodium hydrogen carbonate. After filtration the solid precipitate is washed to chloride-free with water and dried. The crude product obtained is recrystallized from n-hexane under clarifying by activated carbon to give the title compound in 80.6% yield, m.p.: 65°-67° C.

Workup

  1. customthe reaction mixture is evaporated in a water bath of 40° to 50° C. temperature under reduced pressure
  2. additionAfter adding 200 ml of water to the evaporation residue the base
  3. filtrationAfter filtration the solid precipitate
  4. washis washed to chloride-free with water
  5. customdried
  6. customThe crude product obtained
  7. customis recrystallized from n-hexane under clarifying by activated carbon

Sources & evidence

ORD record
ord-f96868f33eb04fbf9eed659dcf49057a
Source dataset
uspto-grants-1992_10
Patent number
US05157038

Reaction notes

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