Hydrochloric Acid → Methyl 4-[2-(methylamino)ethyl]benzoate

HRID 587924Notes

Reaction equation

HRID 587924 reaction equation
[H-].[Na+].FC(F)(F)[C:5]([N:7]([CH2:9][CH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)C)=O.O.Cl>CO.C1COCC1>[CH3:5][NH:7][CH2:9][CH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24758Sodium hydrideHCID 86643732methyl 4-(2-(2,2,2-trifluoro-N-methylacetamido)ethyl)benzoate

Product 1

HCID 21623940Methyl 4-[2-(methylamino)ethyl]benzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22 °C

Procedure

A solution of 0.80 g (5.5 mmol) of sodium hydride (60% mineral oil dispersion) dissolved in 20 mL of methanol was prepared and added to a separate solution of 1.05 g (3.64 mmol) of methyl 4-(2-(2,2,2-trifluoro-N-methylacetamido)ethyl)benzoate dissolved in 12 mL of THF at 0° C. The solution was warmed to 22° C. and stirred for about 36 h. Water was added (100 mL) and the solution was acidified to pH 1 with 1 N HCl. The mixture was washed with DCM (2×100 mL) and then basified with 1 N NaOH to pH 8-9. The aqueous solution was extracted with DCM (3×100 mL) and the organic extracts dried (Na2SO4) and evaporated to give 2b as a white solid which was used without further purification in the subsequent transformation.

Workup

  1. customwas prepared
  2. washThe mixture was washed with DCM (2×100 mL)
  3. extractionThe aqueous solution was extracted with DCM (3×100 mL)
  4. dry with materialthe organic extracts dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-ad81e2da4137490eb035db93246cacb1
Source dataset
uspto-grants-2016_01
Patent number
US09227918B2

Reaction notes

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