Hydrochloric Acid → 2-(Morpholine-4-carbonyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine

HRID 2301117Notes

Reaction equation

HRID 2301117 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15]([C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[O:18])=[CH:16][C:10]=2[CH2:9]1)=O)(C)(C)C.Cl>>[N:19]1([C:17]([C:15]2[S:14][C:11]3[CH2:12][CH2:13][NH:8][CH2:9][C:10]=3[CH:16]=2)=[O:18])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 18377350HCID 18377350, compound

Product 1

HCID 183773652-(Morpholine-4-carbonyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine

Procedure

5-t-Butoxycarbonyl-2-(morpholine-4-carbonyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (610 mg, 1.7 mmol) was mixed with hydrochloric acid-saturated methanol and stirred at room temperature for two nights. The solvent was removed by evaporation from the reaction solution under a reduced pressure, and the residue was mixed with sodium hydroxide aqueous solution (1 N). The reaction product was extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried with anhydrous magnesium sulfate. By evaporating the solvent from the organic layer under a reduced pressure, 270 mg (1.1 mmol, 63% in yield) of the title compound was obtained.

Workup

  1. customThe solvent was removed by evaporation from the reaction solution under a reduced pressure
  2. additionthe residue was mixed with sodium hydroxide aqueous solution (1 N)
  3. extractionThe reaction product was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customBy evaporating the solvent from the organic layer

Sources & evidence

ORD record
ord-8adf94fb09e54db4b19d131bd47e116c
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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