Formaldehyde → HCID 86738228, compound

HRID 851054Notes

Reaction equation

HRID 851054 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C@H:7]2[CH2:12][CH2:11][NH:10][CH2:9][C@H:8]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C=O.[OH-].[Na+].[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29]>CCOCC.C(O)C.C(O)=O>[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29].[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C@H:7]2[CH2:12][CH2:11][N:10]([CH3:25])[CH2:9][C@H:8]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:19][CH:20]=1

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 444972Fumaric AcidHCID 13039291HCID 13039291, compound

Product 1

HCID 86738228HCID 86738228, compound

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 2.4 g of cis-4-(4-bromophenoxy)-3-phenylpiperidine, 7.2 ml of 100% formic acid and 0.81 ml of 37% aqueous formaldehyde solution is refluxed for one hour under nitrogen, cooled and made basic with 35 ml of 10% aqueous sodium hydroxide solution. The mixture is extracted with ether (2×50 ml), the ether extracts are washed with saturated sodium chloride solution, dried overnight over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford a yellow oil. The oil is dissolved in 50 ml of ether and treated dropwise with stirring with a solution of 0.89 g of fumaric acid in a mixture of 75 ml of ether and 15 ml of absolute ethanol. The colorless, fine crystals which precipitate are filtered, washed with ether and dried to afford solid product, mp 172° C. dec.

Workup

  1. temperatureis refluxed for one hour under nitrogen
  2. temperaturecooled
  3. extractionThe mixture is extracted with ether (2×50 ml)
  4. washthe ether extracts are washed with saturated sodium chloride solution
  5. dry with materialdried overnight over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a yellow oil
  9. additiontreated dropwise
  10. filtrationThe colorless, fine crystals which precipitate are filtered
  11. washwashed with ether
  12. customdried
  13. customto afford solid product, mp 172° C. dec.

Sources & evidence

ORD record
ord-9d2bbc29f81d40429d6f42c5dd71a17e
Source dataset
uspto-grants-1983_05
Patent number
US04382141

Reaction notes

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