Hydrochloric Acid → (+)-Epibatidine dihydrochloride

HRID 1107454Notes

Reaction equation

HRID 1107454 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 1.0M 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). δ 3.40 (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-4d6ec82eb31a4bf2ba1c15fd54bc8be9
Source dataset
uspto-grants-2000_05
Patent number
US06060473

Reaction notes

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