Acetic Acid → 3,5-dimethyl-4-morpholin-4-ylmethyl-1H-pyrrole-2-carbaldehyde

HRID 1828895Notes

Reaction equation

HRID 1828895 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1[CH:8]=[O:9].[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.C=O.[C:18](O)(=O)C>C([O-])(O)=O.[Na+]>[CH3:1][C:2]1[C:6]([CH2:18][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[C:5]([CH3:7])[NH:4][C:3]=1[CH:8]=[O:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 8083MorpholineHCID 2704653,5-Dimethyl-1H-pyrrole-2-carbaldehyde

Product 1

HCID 220597173,5-dimethyl-4-morpholin-4-ylmethyl-1H-pyrrole-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

3,5-Dimethylpyrrole-2-carboxaldehyde (0.5 g, 4 mmole) was added to a solution of morpholine (0.35 g, 4 mmol), formaldehyde 37% (0.32 g, 4 mmol) and acetic acid (2 ml). The mixture was stired overnight at room temperature under nitrogen, then the reaction was diluted with NaHCO3 to pH 8. The aqueous solution was extracted with ethylacetate and the organic layer was dried over Mg SO4. The ethylacetate was evaporated in vacuo to give 0.4 g of pure solid.

Workup

  1. extractionThe aqueous solution was extracted with ethylacetate
  2. dry with materialthe organic layer was dried over Mg SO4
  3. customThe ethylacetate was evaporated in vacuo

Sources & evidence

ORD record
ord-92e903755a7243e8830a1cffba3a5171
Source dataset
uspto-grants-2006_06
Patent number
US07060822B1

Reaction notes

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