Pyridine → HCID 86641066, compound

HRID 383940Notes

Reaction equation

HRID 383940 reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][C:11]([CH2:16][CH2:17]O)([OH:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.CCOC(C)=O>C(Cl)Cl>[CH3:35][C:25]1[CH:30]=[CH:29][C:28]([S:31]([O-:15])(=[O:33])=[O:32])=[CH:27][CH:26]=1.[CH2:1]([N+:8]12[CH2:17][CH2:16][C:11]([OH:15])([CH2:10][CH2:9]1)[CH2:12][CH2:13][CH2:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 59291423HCID 59291423, compound

Product 1

HCID 86641066HCID 86641066, compoundYield 114.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-benzyl-4-(2-hydroxyethyl)azepan-4-ol (2.0 g) in DCM (20 mL) were added pyridine (4 mL) and p-toluenesulfonylchloride (1.68 g) at 0° C., followed by stirring at 0° C. for 3 hours and then at room temperature for overnight. The reaction mixture was concentrated under reduced pressure, alkalified by addition of a saturated aqueous NaHCO3 solution, and then extracted with EtOAc. The organic layer was washed with water and brine in this order, dried over MgSO4, and then concentrated under reduced pressure to obtain a pale red solid. EtOAc was added thereto and the solid was pulverized and collected by filtration to obtain 1-benzyl-5-hydroxy-1-azoniabicyclo[3.2.2]nonane 4-methylbenzenesulfonate (1.85 g) as a pale red powder.

Workup

  1. waitat room temperature for overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionalkalified by addition of a saturated aqueous NaHCO3 solution
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with water and brine in this order
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customto obtain a pale red solid
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-e9f1a704999047e6bc2795cd4a3b770c
Source dataset
uspto-grants-2013_02
Patent number
US08367696B2

Reaction notes

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