1-Butanol → HCID 23036275, compound

HRID 1193695Notes

Reaction equation

HRID 1193695 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[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[CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:34])[CH3:33])=[CH:28][C:27]=1[O:35][CH3:36].C(O)CCC.[C:42]([OH:47])(=[O:46])[C:43]([OH:45])=[O:44]>CO.[I-].[K+].C(OCC)C>[C:42]([OH:47])(=[O:46])[C:43]([OH:45])=[O:44].[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:9]2[CH2:10][CH2:11][N:12]([CH2:22][CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][C:29]([C:32](=[O:34])[CH3:33])=[CH:28][C:27]=3[O:35][CH3:36])[CH2:13][CH2:14]2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 2631-ButanolHCID 971Oxalic AcidHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenoneHCID 14407163HCID 14407163, compound

Product 1

HCID 23036275HCID 23036275, compoundYield 68.9%

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 4.42 g (0.0164 mole) of 4-[(4-fluorophenyl)phenylmethyl]piperidine and 4.11 g (0.0170 mole) of 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone, 0.01 g of potassium iodide and 1-butanol was refluxed for 18 hr. The solvent was removed in vacuo, and the residue was partitioned between methylene chloride and dilute sodium hydroxide. The solvent was removed in vacuo to give an oil. A solution of the oil in methanol was treated with an equivalent of oxalic acid, ethyl ether was added, and 6.39 g (68.9%) of white crystalline solid, m.p. 161°-163° C. was obtained.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between methylene chloride and dilute sodium hydroxide
  3. customThe solvent was removed in vacuo
  4. customto give an oil
  5. additionwas added

Sources & evidence

ORD record
ord-4a92052de0084adba82818ec9ce3a8fa
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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