1-Butanol → HCID 23036361, compound

HRID 1709905Notes

Reaction equation

HRID 1709905 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.Cl[CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33](=O)[CH3:34])=[C:29]([O:36][CH3:37])[CH:28]=1.[C:38](=[O:41])([O-:40])[O-:39].[K+].[K+].[I-].[K+].C([OH:50])CCC>>[C:37]([OH:36])(=[O:50])[C:38]([OH:40])=[O:41].[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:9]2[CH2:14][CH2:13][N:12]([CH2:23][CH2:24][CH2:25][O:26][C:27]3[CH:28]=[CH:29][C:30]([CH2:33][CH3:34])=[CH:31][C:32]=3[O:39][CH3:38])[CH2:11][CH2:10]2)=[CH:20][CH:19]=1

Participants

6

Reactant 5

HCID 2631-ButanolHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 132505444-[Bis(4-fluorophenyl)methyl]piperidineHCID 144071823-(p-Acetyl-m-methoxyphenoxy)propyl chloride

Product 1

HCID 23036361HCID 23036361, compoundYield 73.4%

Procedure

A mixture of 4-[bis(4-fluorophenyl)methyl]piperidine (5.74 g, 0.024 mole), 1-[4-(3-chloropropoxy)-2-methoxyphenyl]ethanone (5.57 g, 0.024 mole), and potassium carbonate (5.54 g, 0.04 mole) was heated overnight at gentle reflux in 350 ml of 1-butanol containing potassium iodide (0.2 g). The reaction mixture was concentrated to dryness. The residue was partitioned several times between chloroform and water. The chloroform layer was back extracted with water and 5% sodium hydroxide. The chloroform layer was dried over sodium sulfate, filtered, and solvent removed to give an oil. The oil was converted to the oxalate salt and recrystallized from methanol-ethyl ether. A white solid was obtained and dried overnight in vacuo at 80° C. to give 10.04 g (73.4% yield) of white, crystalline product, mp 185°-186° C.

Workup

  1. temperaturewas heated overnight
  2. concentrationThe reaction mixture was concentrated to dryness
  3. customThe residue was partitioned several times between chloroform and water
  4. extractionThe chloroform layer was back extracted with water and 5% sodium hydroxide
  5. dry with materialThe chloroform layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customsolvent removed
  8. customto give an oil
  9. customrecrystallized from methanol-ethyl ether
  10. customA white solid was obtained
  11. customdried overnight in vacuo at 80° C.
  12. customto give 10.04 g (73.4% yield) of white, crystalline product, mp 185°-186° C.

Sources & evidence

ORD record
ord-64289cc1fd7b4662baa96168c02eb8c2
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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