1-Butanol → HCID 23036346, compound

HRID 1709876Notes

Reaction equation

HRID 1709876 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:32](=[O:35])([OH:34])[O-].[Na+].C([OH:41])CCC>>[C:26]([OH:41])(=[O:25])/[CH:27]=[CH:28]/[C:32]([OH:34])=[O:35].[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]2[CH2:9][CH2:10][N:11]([CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 2631-ButanolHCID 70986(4-Bromobutoxy)benzeneHCID 882784-BenzhydrylpiperidineHCID 516892Sodium Bicarbonate

Product 1

HCID 23036346HCID 23036346, compound

Procedure

A solution of 6.99 g (0.0278 mole) of 4-diphenylmethylpiperidine, 6.64 g (0.029 mole) of (4-bromobutoxy)benzene and 5 g (0.060 mole) of sodium bicarbonate in 400 ml of 1-butanol was heated at reflux for 11 hr. The solvent was removed in vacuo, an the residue was partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride solution was dried over magnesium sulfate, and the solvent was removed in vacuo to give an oil, the free base of the title compound. The base was dissolved in 500 ml of ether, and a small amount of solid was filtered from the solution. To the filtrate was added a solution of 3.2 g (0.0276 mole) of fumaric acid in 60 ml of methanol. A white precipitate was collected to give 7.97 g (55.7%) of white, crystalline solid, m.p. 146°-147° C.

Workup

  1. temperatureat reflux for 11 hr
  2. customThe solvent was removed in vacuo
  3. customan the residue was partitioned between methylene chloride and dilute sodium hydroxide
  4. dry with materialThe methylene chloride solution was dried over magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customto give an oil

Sources & evidence

ORD record
ord-9dbf15dbbdbc4cc09f8cfa86856e4963
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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