Formaldehyde → HCID 86762278, compound

HRID 241703Notes

Reaction equation

HRID 241703 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[C:12](=[O:15])[CH2:13][CH3:14].[CH2:16]=O.[OH-].[Na+]>C(O)(=O)C.O>[N:1]1([CH2:16][CH:10]2[CH:11]=[N:7][C:8]([C:12](=[O:15])[CH2:13][CH3:14])=[CH:9]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 8083MorpholineHCID 14798Sodium HydroxideHCID 612602-Propionylpyrrole

Product 1

HCID 86762278HCID 86762278, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of morpholine (89.3 mmoles) in acetic acid (50 ml) at 0° C. there are added 1-(1H-pyrrol-2-yl)-propan-1-one (81.2 mmoles) and formaldehyde (89.3 mmoles) 37% in water. The reaction mixture is stirred overnight at ambient temperature. After concentration of the mixture, the solution is brought to alkaline pH (10-12) using 20% aqueous NaOH solution at 0° C. and is then extracted with DCM. The organic phase is washed with water and with saturated aqueous NaCl solution, dried over sodium sulphate, filtered and evaporated to dryness and purified by flash chromatography on silica gel (SiO2; gradient 100% AcOEt to AcOEt/MeOH 9/1) to yield the title product.

Workup

  1. customat 0° C.
  2. extractionis then extracted with DCM
  3. washThe organic phase is washed with water and with saturated aqueous NaCl solution
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. custompurified by flash chromatography on silica gel (SiO2; gradient 100% AcOEt to AcOEt/MeOH 9/1)

Sources & evidence

ORD record
ord-7320cf28921d4f96a9761f9f108fbc46
Source dataset
uspto-grants-2014_02
Patent number
US08653073B2

Reaction notes

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