Formaldehyde → 1-(4-Morpholin-4-ylmethyl-1H-pyrrol-2-yl)-propan-1-one

HRID 44248Notes

Reaction equation

HRID 44248 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][C:10]2[CH:9]=[C:8]([C:12](=[O:15])[CH2:13][CH3:14])[NH:7][CH:11]=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 666361321-(4-Morpholin-4-ylmethyl-1H-pyrrol-2-yl)-propan-1-one

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-3a65209da501428bafe9c0d5ff5c3587
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Reaction notes

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