Formaldehyde → 4-(Morpholin-4-ylmethyl)-1H-pyrrole-2-carbaldehyde

HRID 44245

Reaction equation

HRID 44245 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[NH:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH:12]=[O:13].[CH2:14]=O>C(O)(=O)C>[N:1]1([CH2:14][C:10]2[CH:9]=[C:8]([CH:12]=[O:13])[NH:7][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8083MorpholineHCID 13854Pyrrole-2-carboxaldehyde

Product 1

HCID 866508204-(Morpholin-4-ylmethyl)-1H-pyrrole-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of morpholine (0.38 mole) in acetic acid (120 ml) at 0° C. there is added a solution of 1H-pyrrole-2-carbaldehyde (0.32 mole) in acetic acid (100 ml). Formaldehyde (37% aq., 26 ml) is then added dropwise. The reaction mixture is then stirred for 65 hours at ambient temperature. The mixture is concentrated (about 50 ml) and cooled in an ice bath. The pH of the solution is made alkaline (pH=12) using 20% aqueous sodium hydroxide solution. The product is extracted with dichloromethane (DCM) (3×250 ml). The organic phases are combined. The organic phase obtained is washed with saturated aqueous NaCl solution, dried over sodium sulphate, filtered and evaporated to dryness. The residue obtained (oil) is purified on silica gel (SiO2, gradient DCM/MeOH) to yield the title product.

Workup

  1. concentrationThe mixture is concentrated (about 50 ml)
  2. temperaturecooled in an ice bath
  3. extractionThe product is extracted with dichloromethane (DCM) (3×250 ml)
  4. customThe organic phase obtained
  5. washis washed with saturated aqueous NaCl solution
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe residue obtained (oil)
  10. customis purified on silica gel (SiO2, gradient DCM/MeOH)

Sources & evidence

ORD record
ord-d43d3bea4f914fd88805333bdf9810f7
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Linked notes

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