Hydrochloric Acid → (+)-Epibatidine dihydrochloride

HRID 1383879Notes

Reaction equation

HRID 1383879 reaction equation
[CH:1]1[C:6]([CH:7]2[CH:12]3[NH:13][CH:9]([CH2:10][CH2:11]3)[CH2:8]2)=[CH:5][N:4]=[C:3]([Cl:14])[CH:2]=1.C(N(C(C)C)CC)(C)C.[ClH:24]>C(#N)C.CCOCC>[CH2:10]1[CH:9]2[NH:13][CH:12]([CH:7]([C:6]3[CH:1]=[CH:2][C:3]([Cl:14])=[N:4][CH:5]=3)[CH2:8]2)[CH2:11]1.[ClH:24].[ClH:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 1204(-)-Epibatidine-L-tartrateHCID 81531Diisopropylethylamine

Product 1

HCID 21946437(+)-Epibatidine dihydrochlorideYield 36%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

Racemic-epibatidine 19 (42 mg, 0.2 mmol) was mixed with 77 mg (0.7 mmol) freshly prepared ethyl formamidinate hydrochloride and 129 mg (1.0 mmol) diisopropyl ethylamine in 1 ml acetonitrile. After stirring at room temperature for 48 hours, the mixture was acidified with 1.0 M hydrogen chloride in ether. After evaporation in vacuo, the residue was separated on silica gel preparative thin layer chromatography, using a solvent system of 25% methanol in chloroform, to give 25 mg of the compound 45 as a hygroscopic solid. Yield 36%. MS(CI), 236, 238 (free base M+1). H1-NMR (CD3OD). δ3.40 (M, 1H, H2).

Workup

  1. customAfter evaporation in vacuo
  2. customthe residue was separated on silica gel preparative thin layer chromatography

Sources & evidence

ORD record
ord-95cbbd4344c74418a57f6c0c80634eaf
Source dataset
uspto-grants-2001_07
Patent number
US06255490B1

Reaction notes

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