4-hydroxy-N-methoxy-N-methyl-3-(morpholinomethyl)benzamide → 4-Hydroxy-3-morpholin-4-ylmethyl-benzaldehyde

HRID 2390548Notes

Reaction equation

HRID 2390548 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](N(OC)C)=[O:7])=[CH:4][C:3]=1[CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>C1COCC1.[H-].[Cl-].C1([Zr+2]C2C=CC=C2)C=CC=C1>[OH:1][C:2]1[CH:13]=[CH:12][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH2:14][N:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1

Participants

4

Reactant 1

HCID 866390694-hydroxy-N-methoxy-N-methyl-3-(morpholinomethyl)benzamide

Product 1

HCID 4373904-Hydroxy-3-morpholin-4-ylmethyl-benzaldehyde

Reagents, catalysts & solvents 2

HCID 178420592HCID 178420592, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Bis(cyclopentadienyl)zirconium chloride hydride (4.29 g, 16.27 mmol) was added portionwise over 10 min to a solution of 4-hydroxy-N-methoxy-N-methyl-3-(morpholinomethyl)benzamide (3.8 g, 13.56 mmol) in THF (50 mL), under N2 whilst maintaining the temperature below 20° C. Stirred for 2 h, quenched with saturated potassium sodium tartrate, extracted with EtOAc (3×100 mL), washed with more saturated potassium sodium tartrate and brine, dried (Na2SO4), filtered and evaporated in vacuo. Purified by flash chromatography with EtOAc as eluent to give the sub-title compound as a colourless oil. Yield: 2.1 g

Workup

  1. temperaturewhilst maintaining the temperature below 20° C
  2. customquenched with saturated potassium sodium tartrate
  3. extractionextracted with EtOAc (3×100 mL)
  4. washwashed with more saturated potassium sodium tartrate and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customPurified by flash chromatography with EtOAc as eluent

Sources & evidence

ORD record
ord-4d9c20ca0bab46909bf0b805aa674565
Source dataset
uspto-grants-2012_09
Patent number
US08273774B2

Reaction notes

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