Triethylamine → HCID 14371811, compound

HRID 1381941Notes

Reaction equation

HRID 1381941 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]([CH2:20][C:21](O)=[O:22])([C:17](O)=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][O:25][NH3+:26].[Cl-].C(N(CC)CC)C>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]2([C:17](=[O:18])[N:26]([O:25][CH3:24])[C:21](=[O:22])[CH2:20]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11639O-methylhydroxylammonium chlorideHCID 14371890HCID 14371890, compound

Product 1

HCID 14371811HCID 14371811, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1-benzyloxycarbonyl-4-carboxypiperidin-4-yl)acetic acid (3.64 g) in dimethylformamide (30 ml) dicyclohexylcarbodiimide (2.57 g) was added, and this was followed by stirring at room temperature for 30 minutes. o-Methylhydroxylamine hydrochloride (0.95 g) and triethylamine (1.56 ml) were then added, and this was followed by stirring at room temperature for 30 minutes. The resulting precipitates were removed, and the solvent was evaporated under reduced pressure. To the resulting residual oily compound acetic anhydride (20 ml) and anhydrous sodium acetate (0.39 g) were added, and this was followed by stirring at 100° C. for 30 minutes. After the completion of the reaction, the solvent was removed, and the residual oil was dissolved in 50 ml ethyl acetate. The resulting solution was sequentially washed with a saturated aqueous solution of sodium hydrogencarbonate, 1N hydrochloric acid and water, and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure; the resulting residual solid was recrystallized from ethyl ether-petroleum ether to obtain 2.1 g of a colorless crystal having a melting point of 98° C.

Workup

  1. stirringby stirring at room temperature for 30 minutes
  2. customThe resulting precipitates
  3. customwere removed
  4. customthe solvent was evaporated under reduced pressure
  5. additionTo the resulting residual oily compound acetic anhydride (20 ml) and anhydrous sodium acetate (0.39 g) were added
  6. stirringby stirring at 100° C. for 30 minutes
  7. customAfter the completion of the reaction
  8. customthe solvent was removed
  9. dissolutionthe residual oil was dissolved in 50 ml ethyl acetate
  10. washThe resulting solution was sequentially washed with a saturated aqueous solution of sodium hydrogencarbonate, 1N hydrochloric acid and water
  11. dry with materialdried with anhydrous magnesium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customthe resulting residual solid was recrystallized from ethyl ether-petroleum ether

Sources & evidence

ORD record
ord-897484fe30db4c68984025732b85379a
Source dataset
uspto-grants-1989_02
Patent number
US04804665

Reaction notes

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