Hydrochloric Acid → HCID 21472380, compound

HRID 2294954Notes

Reaction equation

HRID 2294954 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[CH:14]2[CH:19]3[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]3)[CH2:15]2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[ClH:22]>CCOCC>[ClH:22].[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[CH:14]2[CH:19]3[CH2:18][CH2:17][N:16]([CH2:21][CH2:20]3)[CH2:15]2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21472381HCID 21472381, compound

Product 1

HCID 21472380HCID 21472380, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Further elution with the above eluent gave a mixture of E- Z-3-[2-(4-butoxyphenyl)vinyl]quinuclidine (600 mg), followed by pure E-3-[2-(4-butoxyphenyl)vinyl]quinuclidine (Rf=0.19) which was converted to its hydrochloride salt using a solution of hydrogen chloride in ether as described above to give E-3-[2-(4-butoxyphenyl)vinyl]-quinuclidine hydrochloride (120 mg), m.p. 235°-238° C.; microanalysis, found: C, 69.0; H, 8.5; N, 4.1% C19H27NO.HCl.0.5H2O requires: C, 68.98; H, 8.77; N, 4.25%; NMR (DMSO-d6): 0.89-0.97(3H, t), 1.3-1.52(2H, m), 1.62-1.8(3H, m), 1.82-2.1(5H, m), 2.75-2.92(1H, m), 2.98-3.52(5H, m), 3.91-4.01(2H, 6.2-6.34(1H, d of d), 6.41-6.55(1H, d, J=15.98 Hertz), 6.82-6.93(2H, d) and 7.31-7.41 (2H, d); m/Z 286 (M+H).

Workup

  1. washFurther elution with the above eluent
  2. customgave

Sources & evidence

ORD record
ord-677c75e2eda34a7184bc1fbae5622bf3
Source dataset
uspto-grants-1997_11
Patent number
US05691349

Reaction notes

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