Hydrochloric Acid → (4R)-4-methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylic acid

HRID 1748250Notes

Reaction equation

HRID 1748250 reaction equation
[CH3:1][C@H:2]1[N:7]2[C:8]3[CH:9]=[C:10]([C:15]([O:17]CC)=[O:16])[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=[O:20])[NH:4][CH2:3]1.[OH-].[Na+].Cl>C(O)C>[CH3:1][C@H:2]1[N:7]2[C:8]3[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=[O:20])[NH:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67235470ethyl (4R)-4-methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylate

Product 1

HCID 67235445(4R)-4-methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of ethyl (4R)-4-methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-α]indole-7-carboxylate (1.3 g, 4.8 mmol) in ethanol (60 mL) is added 1M NaOH solution (12 mL, 12 mmol). The reaction mixture is refluxed for 1.5 h. Then the reaction mixture is acidified with 1M HCl and ethanol is removed under vacuum. The resulting solid is filtered, washed with water, and dried to afford the title compound (1.1 g, 98%) as a solid.

Workup

  1. temperatureThe reaction mixture is refluxed for 1.5 h
  2. customis removed under vacuum
  3. filtrationThe resulting solid is filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-abce55f5a5ff4a4a94d2de2d14c0c988
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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