1-Butanol → HCID 23036266, compound

HRID 1709914Notes

Reaction equation

HRID 1709914 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl: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:35])[CH3:34])=[CH:29][C:28]=1[O:36][CH3:37].[C:38](=[O:41])([O-:40])[O-].[K+].[K+].[I-].[K+].C([OH:50])CCC>>[OH2:26].[C:37]([OH:36])(=[O:50])[C:38]([OH:40])=[O:41].[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl: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]([C:33](=[O:35])[CH3:34])=[CH:29][C:28]=3[O:36][CH3:37])[CH2:11][CH2:10]2)=[CH:20][CH:19]=1

Participants

6

Reactant 5

HCID 2631-ButanolHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenoneHCID 15093840HCID 15093840, compound

Product 1

HCID 23036266HCID 23036266, compoundYield 30%

Procedure

A mixture of 4-[bis(4-chlorophenyl)methyl]piperidine (11.39 g, 0.0357 mole), 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (8.64 g, 0.0357 mole), and potassium carbonate (5.54 g, 0.04 mole) was heated overnight at reflux in 300 ml of 1-butanol containing potassium iodide (0.2 g). The reaction mixture was concentrated to dryness, and the residue obtained was partitioned several times between chloroform and water. The chloroform layer was dried over sodium sulfate ad filtered, and the solvent was removed to give a dark brown oil. This oil was converted to the oxalate salt and the salt was recrystallized from methanol-ethyl ether. A yellow solid was isolated and dried in vacuo overnight at 80° C. The yellow solid was next exposed to the atmosphere for 24 hours and submitted for analysis. This procedure produced 6.65 g (30% yield) of light yellow solid, mp 160°-171° C.

Workup

  1. temperaturewas heated overnight
  2. concentrationThe reaction mixture was concentrated to dryness
  3. customthe residue obtained
  4. customwas partitioned several times between chloroform and water
  5. dry with materialThe chloroform layer was dried over sodium sulfate ad
  6. filtrationfiltered
  7. customthe solvent was removed
  8. customto give a dark brown oil
  9. customthe salt was recrystallized from methanol-ethyl ether
  10. customA yellow solid was isolated
  11. customdried in vacuo overnight at 80° C
  12. customThis procedure produced 6.65 g (30% yield) of light yellow solid, mp 160°-171° C.

Sources & evidence

ORD record
ord-6613fcf2602442ffac66d559eade027a
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

Loading…