Formaldehyde → HCID 23469001, compound

HRID 128239Notes

Reaction equation

HRID 128239 reaction equation
Cl.[CH3:2][NH:3][CH3:4].[CH:5]1([N:11]2[CH:15]=[CH:14][CH:13]=[CH:12]2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[CH2:16]=O>C(O)C.O>[CH:5]1([N:11]2[CH:15]=[CH:14][CH:13]=[C:12]2[CH2:2][N:3]([CH3:16])[CH3:4])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 138996051-Cyclohexyl-1H-pyrrole

Product 1

HCID 23469001HCID 23469001, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of dimethylamine hydrochloride (3.76 g) in 40% aqueous formaldehyde (3.5 ml) was added over 30 minutes to a stirred solution of 1-cyclohexylpyrrole in ethanol (25 ml) and the resulting solution was stirred at room temperature for 18 hours. Evaporation of the solution gave a solid which was dissolved in water. The solution was extracted with ether and then basified to pH 9-10 with 1 N sodium hydroxide solution. The resulting oil was extracted with ether (3×50 ml) and the combined ethereal extracts were washed with water and dried (MgSO4). Evaporation of the ether gave an oil which was chromatographed on silica gel. Elution with chloroform gave 1-cyclohexyl-2-(dimethylaminomethyl)pyrrole (5.0 g) as an oil.

Workup

  1. customEvaporation of the solution
  2. customgave a solid which
  3. extractionThe solution was extracted with ether
  4. extractionThe resulting oil was extracted with ether (3×50 ml)
  5. washthe combined ethereal extracts were washed with water
  6. dry with materialdried (MgSO4)
  7. customEvaporation of the ether
  8. customgave an oil which
  9. customwas chromatographed on silica gel
  10. washElution with chloroform

Sources & evidence

ORD record
ord-ae019736782a44238c28b9cc71766876
Source dataset
uspto-grants-1981_03
Patent number
US04259345

Reaction notes

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