Hydrochloric Acid → 3-[(Piperidin-4-yl)oxy]pyridine--hydrogen chloride (1/2)

HRID 2305749Notes

Reaction equation

HRID 2305749 reaction equation
[ClH:1].[NH:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH2:4][CH2:3]1>>[ClH:1].[ClH:1].[NH:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 121122323-(Piperidin-4-yloxy)pyridine

Product 1

HCID 229897273-[(Piperidin-4-yl)oxy]pyridine--hydrogen chloride (1/2)Yield 63.7%

Procedure

Concentrated HCl (2 mL) was added to 3-(4-piperidinyloxy)pyridine (260 mg, 1.459 mmol), and the resulting solution was concentrated by rotary evaporation. Ethanol was added to the residue and removed by rotary evaporation to dry the product. The procedure was repeated several times until a solid was obtained. The resulting material was recrystallized from 2-propanol. The solids were filtered and dried under vacuum to afford 233 mg (63.7%) of an off-white solid, mp 152-155° C. The compound exhibits a Ki of 592 nM; the effect at muscle sites is 16 percent; and the effect at ganglia sites is 9 percent.

Workup

  1. concentrationthe resulting solution was concentrated by rotary evaporation
  2. additionEthanol was added to the residue
  3. customremoved by rotary evaporation
  4. customto dry the product
  5. customwas obtained
  6. customThe resulting material was recrystallized from 2-propanol
  7. filtrationThe solids were filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-140fc366125f432cb72696e75747ad77
Source dataset
uspto-grants-2002_08
Patent number
US06441006B2

Reaction notes

Loading…