Pyridine → HCID 68749116, compound

HRID 1434724Notes

Reaction equation

HRID 1434724 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CC=CC=1.[CH:20]12[NH:27][CH:24]([CH2:25][CH2:26]1)[CH2:23][CH2:22][CH2:21]2>ClCCl.Cl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:24]23[NH:27][CH:20]([CH2:26][CH2:25]2)[CH2:21][CH2:22][CH2:23]3)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 74044-Nitrobenzenesulfonyl chlorideHCID 1360978-Azabicyclo(3.2.1)octane

Product 1

HCID 68749116HCID 68749116, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-nitrobenzenesulfonyl chloride (1.78 g, 8.0 mmol), pyridine (0.78 mL, 9.6 mmol), and 8-azabicyclo[3.2.1]octane (0.796 g, 8.02 mmol) in dichloromethane (22 mL) was stirred for 5 hrs at 0° C., diluted with 1N HCl, and extracted with dichloromethane. The isolated organic layer was dried (Na2SO4), filtered, concentrated, and triturated with diethyl ether to give 1-(4-nitro-benzenesulfonyl)-8-azabicyclo[3.2.1]octane as a brown solid. The solid was added to a mixture of HCO2NH4 (1.91 g, 30.3 mmol) and 10% Pd/C (catalytic amount) in methanol (20 mL) and ethyl acetate (4 mL), stirred overnight at about 25° C., filtered, concentrated, diluted with water, and extracted with dichloromethane. The isolated organic layer was dried (Na2SO4), filtered and concentrated to give the title compound. 1H NMR (300 MHz, CDCl3) δ 7.74 (d, 2H), 7.02 (d, 2H), 4.17 (brs, 2H), 1.42-1.86 (m, 10H).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe isolated organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-c7491c4c806d4b0aa053d0608cb852fa
Source dataset
uspto-grants-2009_11
Patent number
US07615570B2

Reaction notes

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