Sodium Carbonate → HCID 67069920, compound

HRID 969985Notes

Reaction equation

HRID 969985 reaction equation
[OH:1][CH:2]1[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.[H-].[Na+].Cl[C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][N:14]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([O:1][CH:2]2[CH:7]3[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]3)[CH2:3]2)=[N:14][CH:15]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 15381(+-)-3-QuinuclidinolHCID 24758Sodium hydrideHCID 27344145-Bromo-2-chloropyridine

Product 1

HCID 67069920HCID 67069920, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

3-Hydroxy quinuclidine (Aldrich, 3.2 g, 25 mmol) in DMF (anhydrous, 30 mL) was treated with NaH (Aldrich, 99%, 1.2 g, 50 mmol) at ambient temperature for 1 hour. The mixture was then treated with 2-chloro-5-bromopyridine (7.1 g, 30 mmol) and stirred at 100° C. for 6 hours. The mixture reaction was treated with Na2CO3 (2M, 10 mL) at 10° C. and extracted with ethyl acetate (2×50 mL). The extracts were combined and concentrated under reduced pressure. The title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:2, Rf. 0.20) as oil (5.3 g, yield, 75%). 1H NMR (MeOH-d4, 300 MHz) δ 1.46-1.58 (m, 1H), 1.60-1.88 (m, 2H), 1.96-2.10 (m, 1H), 2.24-2.30 (m, 1H), 2.72-2.98 (m, 5H), 3.42-3.46 (m, 1H), 5.00-5.08 (m, 1H), 6.75 (d, J=8.8 Hz, 1H), 7.77 (dd, J=8.9, 2.4 Hz, 1H), 8.16 (d, J=2.7, 1H) ppm. MS (DCl/NH3) m/z 283 (M+H)+, 285 (M+H)+.

Workup

  1. customThe mixture reaction
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. concentrationconcentrated under reduced pressure
  4. customThe title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:2, Rf. 0.20) as oil (5.3 g, yield, 75%)

Sources & evidence

ORD record
ord-b28d3fce479c417babf18ecd2d2ad6e9
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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