4-Bromopyridine → HCID 18966429, compound

HRID 2226149Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.[N:13]12[CH2:20][CH2:19][CH:16]([CH2:17][CH2:18]1)[C:15](=[O:21])[CH2:14]2>>[OH:21][C:15]1([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[CH:16]2[CH2:19][CH2:20][N:13]([CH2:18][CH2:17]2)[CH2:14]1

Participants

Reactant 3

HCID 142684-Bromopyridine

HCID 195073-Quinuclidinone

HCID 178418339Butyllithium

Product 1

HCID 18966429HCID 18966429, compoundYield 56.8%

Procedure

By the procedure described in Description 1, n-butyl lithium (1.6M in hexanes, 19.5 ml, 31.2 mmol), 4-bromopyridine (5.37 g, 34.0 mmol) and 3-quinuclidinone (3.90 g, 31.2 mmol) gave 3.62 g of the title compound as a tan powder. The dihydrochloride salt was prepared; m.p. 225°-235° C.; Found: C, 50.50; H, 6.39; N, 9.76. C12G20N2, Cl2O.0.5H2O requires C, 50.36; H, 6.69; N, 9.79; δ(360 MHz, D2O) 8.854 (2H, d, J=6.8 Hz, py-H), 8.207 (2H, d, J=6.8 Hz, py-H), 4.016 (1H, d, J=14.2 Hz, H-2ax), 3.696 (1H, d, J=14.2 Hz, H-2eq), 3.52-3.30 (4H, m, H2 -6 and H2 -7), 2.70-1.60 (5H, m, H-4, H2 -5 and H2 -8); m/e 204 (M+).

Sources & evidence

ORD record: ord-0a4211458a93443eb6ed777f095216f7
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05346906

Reaction notes

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