Hydrochloric Acid → HCID 59323466, compound

HRID 2390058Notes

Reaction equation

HRID 2390058 reaction equation
C[O:2][C:3]([C:5]1[CH:32]=[CH:31][C:8]([CH2:9][NH:10][CH2:11][CH2:12][N:13]2[CH:22]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14]2)=[CH:7][CH:6]=1)=[O:4].Cl>[OH-].[Na+].C(O)C>[F:30][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][CH:22]2[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][N:13]2[CH2:12][CH2:11][NH:10][CH2:9][C:8]2[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:32][CH:31]=2)=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59323251HCID 59323251, compound

Product 1

HCID 59323466HCID 59323466, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

9 mg of N-(4-methoxycarbonylbenzyl)-2-[3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine obtained in Example 108 was dissolved in 1 mL of 2.5 N aqueous sodium hydroxide solution and 1 mL of ethanol, followed by stirring at 0° C. for 3 hours. After completion of the reaction, 2N hydrochloric acid was added to the reaction liquid, followed by extraction with chloroform, and the organic layer was then washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 6 mg (yield 76%) of a title compound as a pale yellow oily substance.

Workup

  1. additionwas added to the reaction liquid
  2. extractionfollowed by extraction with chloroform
  3. washthe organic layer was then washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c488a755cd8644cfa2d3da779e035d21
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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