Hydrogen chloride-ethyl acetate → 6-bromo-1-oxo-4-phenyl-2-(piperidin-2-ylmethyl)-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester Hydrochloride

HRID 750140Notes

Reaction equation

HRID 750140 reaction equation
C(OC(=O)C)C.[ClH:7].[CH3:8][O:9][C:10]([C:12]1[N:13]([CH2:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][N:32]2C(OC(C)(C)C)=O)[C:14](=[O:29])[C:15]2[C:20]([C:21]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:19][C:18]([Br:28])=[CH:17][CH:16]=2)=[O:11]>>[ClH:7].[CH3:8][O:9][C:10]([C:12]1[N:13]([CH2:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][NH:32]2)[C:14](=[O:29])[C:15]2[C:20]([C:21]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:19][C:18]([Br:28])=[CH:17][CH:16]=2)=[O:11]

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 691559506-bromo-2-(1-tert-butoxycarbonylpiperidin-2-ylmethyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

Product 1

HCID 691563966-bromo-1-oxo-4-phenyl-2-(piperidin-2-ylmethyl)-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester HydrochlorideYield 53%

Procedure

4N Hydrogen chloride ethyl acetate solution (5 ml) was added to 6-bromo-2-(1-tert-butoxycarbonylpiperidin-2-ylmethyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (44 mg), and the mixture was stirred at room temperature for 2 hrs. The solvent was evaporated under reduced pressure, and the obtained residue was crystallized from isopropyl ether to give the title compound (21 mg, 53%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe obtained residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-b58a3c7320a84cefaf418f4de3970330
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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