Ethyl Bromide → HCID 19887574, compound

HRID 654517Notes

Reaction equation

HRID 654517 reaction equation
[Cl-:1].[CH2:2]([N+:9]12[CH2:16][C:13]([OH:17])([CH2:14][CH2:15]1)[CH2:12][CH2:11][CH2:10]2)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[Na+].Br[CH2:21][CH3:22]>CN(C=O)C>[Cl-:1].[CH2:2]([N+:9]12[CH2:16][C:13]([O:17][CH2:21][CH3:22])([CH2:14][CH2:15]1)[CH2:12][CH2:11][CH2:10]2)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 19887580HCID 19887580, compound

Product 1

HCID 19887574HCID 19887574, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-benzyl-5-hydroxy-1-azoniabicyclo[3.2.1]octane chloride (D7a, 3.05 g, 0.012 mole) in dry DMF (100 ml) under nitrogen was treated with sodium hydride (600mg of 80% oil dispersion, 0.020 mole) and stirred at room temperature for 40 min. The mixture was then treated with bromoethane (4.7 ml, 0.063 mole) and stirred at room temperature for 16h. The excess sodium hydride was destroyed by addition of ethanol (5 ml) and the mixture acidified with glacial acetic acid (5 ml) and then concentrated in vacuo to give an orange semi-solid containing the title compound (D8). This was used in the next step without any purification.

Workup

  1. stirringstirred at room temperature for 16h
  2. customThe excess sodium hydride was destroyed by addition of ethanol (5 ml)
  3. concentrationconcentrated in vacuo
  4. customto give an orange semi-solid
  5. customThis was used in the next step without any purification

Sources & evidence

ORD record
ord-45bce58d0dcd493b977bdba457bbebd4
Source dataset
uspto-grants-1992_07
Patent number
US05132316

Reaction notes

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