Hydrochloric Acid → trans-3,4-Dimethyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylic acid

HRID 1748260Notes

Reaction equation

HRID 1748260 reaction equation
[CH3:1][C@H:2]1[C@H:19]([CH3:20])[N:6]2[C:7]3[CH:8]=[C:9]([C:14]([O:16]CC)=[O:15])[CH:10]=[CH:11][C:12]=3[CH:13]=[C:5]2[C:4](=[O:21])[NH:3]1.[OH-].[Na+].Cl>C(O)C>[CH3:1][C@H:2]1[C@H:19]([CH3:20])[N:6]2[C:7]3[CH:8]=[C:9]([C:14]([OH:16])=[O:15])[CH:10]=[CH:11][C:12]=3[CH:13]=[C:5]2[C:4](=[O:21])[NH:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86682387Ethyl trans-3,4-dimethyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylate

Product 1

HCID 67235436trans-3,4-Dimethyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylic acidYield 94.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
80 °C

Procedure

To a suspension of ethyl trans-3,4-dimethyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylate (930 mg, 3.2 mmol) in ethanol (40 mL) is added 1M NaOH solution (10 mL, 10 mmol). The reaction mixture is heated at 80° C. for 1 h and then cooled to room temperature. The reaction mixture is acidified using concentrated HCl and ethanol is removed under vacuum. The resulting solid is filtered, rinsed with water and dried to afford the title compound (782 mg, 93%).

Workup

  1. temperaturecooled to room temperature
  2. customis removed under vacuum
  3. filtrationThe resulting solid is filtered
  4. washrinsed with water
  5. customdried

Sources & evidence

ORD record
ord-81d043db83904b2aa9d229269ecccc2f
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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