1-Butanol → HCID 23036370, compound

HRID 1709886Notes

Reaction equation

HRID 1709886 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, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 6.10 g (0.021 mole) of 4-[bis(4-fluorophenyl)methyl]piperidine and 4.53 g (0.021 mole of 4-(3-chloropropoxy)benzamide in 350 ml of 1-butanol containing potassium carbonate (5.53 g, 0.021 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 methanol-ethyl 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 methanol-ethyl ether
  10. customThe white, crystalline solid obtained
  11. customwas dried in vacuo overnight at 65° C
  12. customA yield of 5.47 g (40.3%) of white, crystalline product was obtained

Sources & evidence

ORD record
ord-367d1c8466e546e4b61e16bea5b40de9
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

Loading…