Formic Acid → HCID 13423997, compound

HRID 1980254Notes

Reaction equation

HRID 1980254 reaction equation
[ClH:1].[O:2]([CH2:9][C:10]1([OH:16])[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:17](O)=O.C=O.[OH-].[Na+]>O>[ClH:1].[CH3:17][N:12]1[CH2:13][CH2:14][CH2:15][C:10]([CH2:9][O:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)([OH:16])[CH2:11]1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 13424001HCID 13424001, compound

Product 1

HCID 13423997HCID 13423997, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 5 g (0.024 mole) of crude 3-(phenoxymethyl)-3-piperidinol monohydrochloride and 5 g (0.096 mole) of formic acid (88%) in 10 ml of water was treated with 3 ml (0.036 mole) of formalin (37%) and heated on a steam bath for 18 hours. The reaction mixture was diluted with water, made basic with 3N sodium hydroxide, and extracted with three 40 ml portions of methylene chloride. The extracts were combined over magnesium sulfate, filtered, and evaporated under reduced pressure to give a pale yellow oil (4.2 g). The oil was chromatographed on a 400 g column of florisol using an acetone-benzene gradient (0-2%) to elute the product. Fractions containing nearly pure product were combined and evaporated under reduced pressure. The residual oil was dissolved in acetone, treated with ethereal hydrogen chloride and allowed to stand overnight. Filtration afforded 1.8 g solid, which was recrystallized from cold acetone (charcoal pretreatment) to give 1.3 g of hydrochloride salt, m.p. 151° -152° C.

Workup

  1. temperatureheated on a steam bath for 18 hours
  2. extractionextracted with three 40 ml portions of methylene chloride
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0daeded458454d75a9d4becfb350e17c
Source dataset
uspto-grants-1985_04
Patent number
US04508724

Reaction notes

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