Hydrochloric Acid → HCID 67743539, compound

HRID 2396742Notes

Reaction equation

HRID 2396742 reaction equation
[H-].[Na+].Br[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]3[O:17][CH2:18][O:19][C:13]=3[CH:12]=2)=[CH:7][CH:6]=1.[OH2:20].[ClH:21].[CH3:22][N:23]([CH:25]=O)[CH3:24]>CC(C)=O.CCOCC>[ClH:21].[O:17]1[C:14]2[CH:15]=[CH:16][C:11]([C:8]3[CH:9]=[CH:10][C:5]([CH2:4][O:20][CH:4]4[CH:5]5[CH2:10][CH2:22][N:23]([CH2:24][CH2:6]5)[CH2:25]4)=[CH:6][CH:7]=3)=[CH:12][C:13]=2[O:19][CH2:18]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 6228Dimethylformamide3×HCID 24758Sodium hydrideHCID 20095431HCID 20095431, compound

Product 1

HCID 67743539HCID 67743539, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 0.14 g (3.44 m mole) of 60% sodium hydride in 20 ml of anhydrous DMF is added a solution of 0.48 g (3.44 m mole) of 3-quinuclidinol borane complex in 10 ml of DMF dropwise over 3 minutes. The mixture is stirred at room temperature for 15 minutes and a solution of 1.0 g (3.44 m moles) of 4-bromomethyl-3', 4'-methylenedioxy-1,1-biphenyl in 10 ml of DMF was added dropwise over 5 minutes. The mixture is stirred at room temperature for 2 hours and poured into 75 ml of water and extracted with 150 ml of ether. The ether is washed with water, dried over magnesium sulfate and filtered. The filtrate is evaporated and the residue purified by flash chromatography using 4:1 hexane:ethyl acetate to give a solid with 100°-3° mp. This solid is suspended in 10 ml of acetone and ethanolic hydrochloric acid is added to pH1. The mixture is stirred at room temperature for 15 minutes and then diluted with ether to precipitate 3-[4-(1,3-benzodioxol-5-yl) benzyloxy]-1-azabicyclo[2.2.21octane hydrochloride (m.p. 195°-8°).

Workup

  1. stirringThe mixture is stirred at room temperature for 2 hours
  2. extractionextracted with 150 ml of ether
  3. washThe ether is washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate is evaporated
  7. customthe residue purified by flash chromatography
  8. customethyl acetate to give a solid with 100°-3° mp. This solid
  9. stirringThe mixture is stirred at room temperature for 15 minutes
  10. customto precipitate 3-[4-(1,3-benzodioxol-5-yl) benzyloxy]-1-azabicyclo[2.2.21octane hydrochloride (m.p. 195°-8°)

Sources & evidence

ORD record
ord-98fb472f7b8c401e920a3df51b91ee87
Source dataset
uspto-grants-1996_02
Patent number
US05494918

Reaction notes

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