Hydrochloric Acid → HCID 13741757, compound

HRID 1290887Notes

Reaction equation

HRID 1290887 reaction equation
CO[CH:3]1[CH2:7][CH2:6][CH:5]([O:8]C)O1.Cl.[CH2:11]1[N:16]([CH2:17][CH2:18][NH2:19])[CH2:15][CH2:14][O:13][CH2:12]1.[CH2:20]([C:27](O)=O)[C:21](CC(O)=O)=O.[OH-].[Na+]>O>[O:13]1[CH2:14][CH2:15][N:16]([CH2:17][CH2:18][N:19]2[CH:7]3[CH2:3][CH2:27][CH:20]2[CH2:21][C:5](=[O:8])[CH2:6]3)[CH2:11][CH2:12]1

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 68328Acetonedicarboxylic acidHCID 790982,5-DimethoxytetrahydrofuranHCID 4082852-Morpholinoethylamine

Product 1

HCID 13741757HCID 13741757, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a solution of 16.2 ml of 2,5-dimethoxytetrahydrofuran in 50 ml of water was added 6 ml of conc. hydrochloric acid. The mixture was stirred at room temperature for 20 minutes. Thereafter, 150 ml of water, 25 ml of 1-(2-aminoethyl)morpholine, 20 ml of conc. hydrochloric acid and 20.1 g of 1,3-acetonedicarboxylic acid were successively added to the reaction mixture. Furthermore, a solution of 8.8 g of Na2HPO4 and 2.5 g of sodium hydroxide in 100 ml of water was added to the mixture. Thereafter the pH was adjusted to the range of 2 to 3. After stirring overnight at room temperature, the reaction solution was washed with chloroform. Potassium carbonate was added to the mixture to render alkaline, followed by extraction with chloroform. The organic layer was washed with water and then dried over anhydrous sodium sulfate. The solvent was then distilled off. The residue was purified by silica gel column chromatography (chloroform:NH3 -saturated methanol=20:1) to give 26.7 g of 8-(2-morpholinoethyl)-8-azabicyclo[3.2.1]octan-3-one.

Workup

  1. stirringAfter stirring overnight at room temperature
  2. washthe reaction solution was washed with chloroform
  3. additionPotassium carbonate was added to the mixture
  4. extractionfollowed by extraction with chloroform
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was then distilled off
  8. customThe residue was purified by silica gel column chromatography (chloroform:NH3 -saturated methanol=20:1)

Sources & evidence

ORD record
ord-45fbed5d83b34f35839bff31dd961b7c
Source dataset
uspto-grants-1998_05
Patent number
US05753673

Reaction notes

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