Formaldehyde → 1-methyl-4-morpholin-4-ylmethyl-1H-pyrrole-2-carbaldehyde

HRID 241704

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

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-b8e32032b06148739d8dbbd510bac55f
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653073B2

Linked notes

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