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

HRID 983068Notes

Reaction equation

HRID 983068 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1[CH:8]=[O:9].[C:10]([OH:13])(=O)[CH3:11]>C1COCC1.O>[CH3:1][C:2]1[C:6]([CH2:5][N:4]2[CH2:11][CH2:10][O:13][CH2:2][CH2:3]2)=[C:5]([CH3:7])[NH:4][C:3]=1[CH:8]=[O:9]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 2704653,5-Dimethyl-1H-pyrrole-2-carbaldehyde

Product 1

HCID 220597173,5-dimethyl-4-morpholin-4-ylmethyl-1H-pyrrole-2-carbaldehydeYield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
92.5 °C

Procedure

A mixture of 3,5-dimethyl-1H-pyrrole-2-carbaldehyde (1.85 g, 15 mmol), di-morpholine-methane (5 mL, 27 mL) in THF (40 mL), water (15 mL) and acetic acid (4 mL) was heated to reflux (oil bath 90-95° C.) for 6 hours. The reaction was concentrated to a volume of 20 mL, basified with Na2CO3 and extracted with ethyl acetate (3×75 mL). The combined extracts were dried, concentrated and the residue was purified on a silica gel column to give 2 g (36%) of 3,5-dimethyl-4-morpholin-4-ylmethyl-1H-pyrrole-2-carbaldehyde as a solid.

Workup

  1. temperaturewas heated
  2. concentrationThe reaction was concentrated to a volume of 20 mL
  3. extractionextracted with ethyl acetate (3×75 mL)
  4. customThe combined extracts were dried
  5. concentrationconcentrated
  6. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-355042b6c1c34fdb83970e36195fcb3e
Source dataset
uspto-grants-2005_03
Patent number
US06861418B2

Reaction notes

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