Potassium Iodide → 3-[1-(3-Hydroxyphenyl)-6-azabicyclo[3.2.1]octan-6-yl]-1-phenylpropan-1-one--hydrogen chloride (1/1)

HRID 1580151Notes

Reaction equation

HRID 1580151 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]23[CH2:15][CH:12]([NH:13][CH2:14]2)[CH2:11][CH2:10][CH2:9]3)[CH:5]=[CH:6][CH:7]=1.[C:16]([CH2:24][CH2:25][Cl:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(Cl)(Cl)Cl.O.CN(C)C=O>[ClH:26].[OH:1][C:2]1[CH:3]=[C:4]([C:8]23[CH2:15][CH:12]([N:13]([CH2:25][CH2:24][C:16](=[O:23])[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH2:14]2)[CH2:11][CH2:10][CH2:9]3)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 702953-ChloropropiophenoneHCID 3045778HCID 3045778, compound

Product 1

HCID 122866683-[1-(3-Hydroxyphenyl)-6-azabicyclo[3.2.1]octan-6-yl]-1-phenylpropan-1-one--hydrogen chloride (1/1)Yield 13.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 0.4 g of 1-(3-hydroxyphenyl)-6-azabicyclo[3,2,1]octane, 0.4 g of 2-benzoylethyl chloride, 0.4 of potassium carbonate, 0.03 g of potassium iodide and 5 ml of dimethylformamide is stirred at 100°C for 4 hours in a nitrogen atmosphere. After cooling, water is added to the mixture, and the aqueous mixture is extracted with chloroform. The chloroform extract is washed with water, dried and then evaporated to remove solvent. The residue thus obtained is dissolved in 5 ml of chloroform. The chloroform solution is poured onto a column of 40 g of silica gel. Then, the column is eluted with a mixture of 300 ml of chloroform and 15 ml of methanol, and the effluent is evaporated to remove solvent. Methanolic hydrogen chloride is added to the residue in ether, and the crystalline precipitate is collected by filtration. The precipitate is recrystallized from a mixture of methanol and ether. 0.1 g of 1-(3-hydroxyphenyl)-6-(2-benzoylethyl)-6-azabicyclo[ 3,2,1]octane hydrochloride is obtained. M.p. 187°- 189°C.

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous mixture is extracted with chloroform
  3. extractionThe chloroform extract
  4. washis washed with water
  5. customdried
  6. customevaporated
  7. customto remove solvent
  8. customThe residue thus obtained
  9. washThen, the column is eluted with a mixture of 300 ml of chloroform and 15 ml of methanol
  10. customthe effluent is evaporated
  11. customto remove solvent
  12. additionMethanolic hydrogen chloride is added to the residue in ether
  13. filtrationthe crystalline precipitate is collected by filtration
  14. customThe precipitate is recrystallized from a mixture of methanol and ether

Sources & evidence

ORD record
ord-c817ba6d6ce54ebea68590f7069c93c4
Source dataset
uspto-grants-1976_01
Patent number
US03932429

Reaction notes

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