Potassium Carbonate → 6-Ethoxycarbonylamino-1-methyl-3,4-dihydroisoquinoline

HRID 1173128Notes

Reaction equation

HRID 1173128 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:8]=1)(=O)[CH3:2].C(=O)([O-])[O-].[K+].[K+]>>[CH2:17]([O:16][C:14]([NH:13][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[C:1]([CH3:2])=[N:4][CH2:5][CH2:6]2)=[O:15])[CH3:18]

Participants

3

Reactant 2

HCID 11430Potassium CarbonateHCID 22674171N-Acetyl-N-(3-ethoxycarbonylaminophenethyl)amine

Product 1

HCID 226741196-Ethoxycarbonylamino-1-methyl-3,4-dihydroisoquinoline

Procedure

Using N-acetyl-N-(3-ethoxycarbonylaminophenethyl)amine (1.0 g, Production Example 30b), a cyclization reaction was run according to the method described in Heterocycles 31 (2), 341 (1990). After the reaction was completed, the reaction solution was poured into ice and basified with potassium carbonate. Then, the solution was extracted with ethyl acetate, and the extract was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, to give the title compound as a brown oil.

Workup

  1. customa cyclization reaction
  2. additionthe reaction solution was poured into ice
  3. extractionThen, the solution was extracted with ethyl acetate
  4. washthe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d9621e8322f34164b9aff0b78474d536
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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