Formaldehyde → 1-methyl-4-morpholin-4-ylmethyl-1H-pyrrole-2-carbaldehyde
Reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:7][N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH:13]=[O:14].[CH2:15]=O>C(O)(=O)C.O>[CH3:7][N:8]1[CH:12]=[C:11]([CH2:15][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[CH:10]=[C:9]1[CH:13]=[O:14].[CH3:7][N:8]1[C:12]([CH2:15][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:11][CH:10]=[C:9]1[CH:13]=[O:14]Participants
Reactant 3
Product 2
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a solution of morpholine (130 mmoles) in acetic acid (60 ml) at 0° C. there are added 1-methyl-1H-pyrrole-2-carbaldehyde (110 mmoles) and formaldehyde (110 mmoles) 37% in water. The reaction mixture is stirred for 16 hours at 50° C. After evaporation to dryness, about 100 ml of 25% aqueous sodium hydroxide solution are added. After extraction with DCM, the organic phase is washed with water and with saturated aqueous NaCl solution, dried over sodium sulphate, filtered and evaporated to dryness. The residue is purified by flash chromatography on silica gel (SiO2; gradient AcOEt/MeOH) to yield the title products 1-methyl-4-morpholin-4-ylmethyl-1H-pyrrole-2-carbaldehyde and 1-methyl-5-morpholin-4-ylmethyl-1H-pyrrole-2-carbaldehyde in a ratio of 1/5.
Workup
- customAfter evaporation to dryness, about 100 ml of 25% aqueous sodium hydroxide solution
- additionare added
- extractionAfter extraction with DCM
- washthe organic phase is washed with water and with saturated aqueous NaCl solution
- dry with materialdried over sodium sulphate
- filtrationfiltered
- customevaporated to dryness
- customThe residue is purified by flash chromatography on silica gel (SiO2; gradient AcOEt/MeOH)
Sources & evidence
- ORD record
- ord-9649336304ea44fb80132f3e1b54a189
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08133889B2
Reaction notes
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