Potassium Iodide → 1-Butanone, 1-(4-fluorophenyl)-4-(1-(3-methoxyphenyl)-6-azabicyclo(3.2.1)oct-6-yl)-, hydrochloride, (+-)-

HRID 1580141Notes

Reaction equation

HRID 1580141 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]23[CH2:16][CH:13]([NH:14][CH2:15]2)[CH2:12][CH2:11][CH2:10]3)[CH:6]=[CH:7][CH:8]=1.[F:17][C:18]1[CH:29]=[CH:28][C:21]([C:22]([CH2:24][CH2:25][CH2:26][Cl:27])=[O:23])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C1(C)C=CC=CC=1>[ClH:27].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]23[CH2:16][CH:13]([N:14]([CH2:26][CH2:25][CH2:24][C:22](=[O:23])[C:21]4[CH:20]=[CH:19][C:18]([F:17])=[CH:29][CH:28]=4)[CH2:15]2)[CH2:12][CH2:11][CH2:10]3)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 3045729HCID 3045729, compound

Product 1

HCID 30457651-Butanone, 1-(4-fluorophenyl)-4-(1-(3-methoxyphenyl)-6-azabicyclo(3.2.1)oct-6-yl)-, hydrochloride, (+-)-Yield 42.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 0.8 g of 1-(3-methoxyphenyl)-6-azabicyclo[ 3,2,1]octane, 0.81 g of 3-(4-fluorobenzoyl)propyl chloride, 0.8 g of potassium carbonate, 0.03 g of potassium iodide and 20 ml of toluene is refluxed for 48 hours. After cooling, the mixture is treated in the same manner as described in Example 11. 0.65 g of 1-(3-methoxyphenyl)-6-[3-(4-fluorobenzoyl)propyl]-6-azabicyclo[3,2,1]octane hydrochloride is obtained. M.p. 195° - 196°C(recrystallized from a mixture of ethanol and ether).

Workup

  1. temperatureis refluxed for 48 hours
  2. temperatureAfter cooling
  3. additionthe mixture is treated in the same manner

Sources & evidence

ORD record
ord-117c200765754eac8354dfb8537612e5
Source dataset
uspto-grants-1976_01
Patent number
US03932429

Reaction notes

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