Hydrochloric Acid → 3-[(3S)-Pyrrolidin-3-yloxy]pyridine dihydrochloride

HRID 1168996Notes

Reaction equation

HRID 1168996 reaction equation
[ClH:1].[NH:2]1[CH2:6][CH2:5][C@H:4]([O:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH2:3]1.C(O)C.CC(O)C>CO>[ClH:1].[ClH:1].[NH:2]1[CH2:6][CH2:5][C@H:4]([O:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3776IsopropanolHCID 121122333-[(3S)-3-Pyrrolidinyloxy]pyridine

Product 1

HCID 700317343-[(3S)-Pyrrolidin-3-yloxy]pyridine dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated HCl (2 mL) was added drop-wise to 3-((3S)-3-pyrrolidinyloxy)pyridine (240 mg, 1.462 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. Ethanol (1 mL) was added, and the resulting solution was treated with hot 2-propanol producing a precipitate. The solution was allowed to cool to ambient temperature and was further cooled at 5° C. for 48 h. The solids were filtered and dried under vacuum at 40° C. for 16 h to afford 215 mg (62.0%) of a hygroscopic, light-brown, granular solid, mp 145-148° C., [α]20.5D+26.67° (c1.0, MeOH). The compound exhibits a Ki of 230 nM.

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. temperaturewas further cooled at 5° C. for 48 h
  7. filtrationThe solids were filtered
  8. customdried under vacuum at 40° C. for 16 h
  9. customto afford 215 mg (62.0%) of a hygroscopic

Sources & evidence

ORD record
ord-25d85fbae1c94659bfd797f40cfc6e3c
Source dataset
uspto-grants-2003_09
Patent number
US06627648B1

Reaction notes

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