1-Butanol → HCID 23036460, compound

HRID 1193700Notes

Reaction equation

HRID 1193700 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]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=1.[C:37](=[O:40])([O-:39])[O-].[K+].[K+].[I-].[K+].C([OH:49])CCC>C(Cl)(Cl)Cl>[C:27]([OH:26])(=[O:49])[C:37]([OH:39])=[O:40].[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:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=3)[CH2:11][CH2:10]2)=[CH:20][CH:19]=1

Participants

7

Reactant 5

HCID 2631-ButanolHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 132505444-[Bis(4-fluorophenyl)methyl]piperidineHCID 14407179HCID 14407179, compound

Product 1

HCID 23036460HCID 23036460, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 6.02 g (0.021 mole) of 4-[bis(4-fluorophenyl)methyl]piperidine and 5.22 g (0.021 mole) of 1-(3-chloropropoxy)-4-(methylsulfonyl)benzene in 350 ml of 1-butanol containing potassium carbonate (5.53 g, 0.04 mole) and potassium iodide (0.2 g) was heated overnight at gentle reflux. The reaction was filtered and stripped to dryness. The residue obtained was dissolved in chloroform and extracted with water. The chloroform layer was dried, filtered, and solvent removed to give an oil. The dark brown oil was converted to the oxalate salt and recrystallized from methanol-diethyl ether to give a white solid. This material was dried in vacuo overnight at 65° C. A yield of 6.21 g (50.1%) of white crystalline solid, m.p. 202°-204° C. was obtained.

Workup

  1. temperaturewas heated overnight at gentle reflux
  2. filtrationThe reaction was filtered
  3. customThe residue obtained
  4. extractionextracted with water
  5. dry with materialThe chloroform layer was dried
  6. filtrationfiltered
  7. customsolvent removed
  8. customto give an oil
  9. customrecrystallized from methanol-diethyl ether
  10. customto give a white solid
  11. customThis material was dried in vacuo overnight at 65° C

Sources & evidence

ORD record
ord-1526aa157f394c8285cf21638e756c0e
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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