HCID 22451508, compound → HCID 22451496, compound

HRID 2185644Notes

Reaction equation

HRID 2185644 reaction equation
[ClH:1].[CH2:2]1[C:10]2[C:5](=[C:6]([O:11][CH:12]3[CH2:15][N:14](C(C4C=CC=CC=4)C4C=CC=CC=4)[CH2:13]3)[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1>C(O)C.[Pd]>[ClH:1].[CH2:2]1[C:10]2[C:5](=[C:6]([O:11][CH:12]3[CH2:13][NH:14][CH2:15]3)[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 22451508HCID 22451508, compound

Product 1

HCID 22451496HCID 22451496, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 3 g of 3-[(2,3-dihydro-1H-inden-4yl)oxy]-1-(diphenylmethyl)-azetidine hydrochloride in 250 ml ethanol were added 600 mg of palladium hydroxyde on carbon powder and the mixture was hydrogenated in a Parr apparatus at 60 psi during 16 hours. After removal of the catalyst and evaporation of the solvent in vacuo the residue was washed several times with diethyl ether and decanted to remove the diphenylmethane formed. The remaining solid was crystallized from ethanol/diethyl ether, yielding 1.27 g of 3-[(2,3-dihydro-1H-inden-4-yl)oxy]-azetidine hydrochloride, m.p. 65° C.

Workup

  1. customAfter removal of the catalyst and evaporation of the solvent in vacuo the residue
  2. washwas washed several times with diethyl ether
  3. customdecanted
  4. customto remove the diphenylmethane
  5. customformed
  6. customThe remaining solid was crystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-e6bf601e95c847adad2bf97708f087d1
Source dataset
uspto-grants-2002_06
Patent number
US06403573B1

Reaction notes

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