1-Butanol → HCID 23036370, compound

HRID 1193699Notes

Reaction equation

HRID 1193699 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:35]=[CH:34][C:30]([C:31]([NH2:33])=[O:32])=[CH:29][CH:28]=1.[C:36](=[O:39])([O-:38])[O-].[K+].[K+].[I-].[K+].C([OH:48])CCC>C(Cl)(Cl)Cl>[C:31]([OH:48])(=[O:32])/[CH:30]=[CH:34]/[C:36]([OH:38])=[O:39].[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:35]=[CH:34][C:30]([C:31]([NH2:33])=[O:32])=[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 144071764-(3-Chloropropoxy)benzamide

Product 1

HCID 23036370HCID 23036370, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 6.10 g (0.02125 mole) of 4-[bis(4-fluorophenyl)methyl]piperidine and 4.53 g (0.02125 mole) of 4-(3-chloropropoxy)benzamide in 350 ml of 1-butanol containing potassium carbonate (5.53 g, 0.02125 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. This material was converted to the fumarate salt and recrystallized from methanoldiethyl ether. The white crystalline solid obtained was dried in vacuo overnight at 65° C. A yield of 5.47 g (40.3%) of white crystalline product was obtained, m.p. 193°-194° C.

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 methanoldiethyl ether
  10. customThe white crystalline solid obtained
  11. customwas dried in vacuo overnight at 65° C

Sources & evidence

ORD record
ord-f18888d0d41a44dcb58509e6dd267478
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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