Hydrogen chloride-ethyl acetate → HCID 68448735, compound

HRID 450796Notes

Reaction equation

HRID 450796 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][N:10]1[CH:19]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[Cl:27])[CH:18]([C:28](=[O:38])[NH:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:39])(C)(C)C.Cl.C(OCC)(=O)C>>[NH2:7][CH2:8][CH2:9][N:10]1[CH:19]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[Cl:27])[CH:18]([C:28]([NH:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:38])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:39]

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 72303539HCID 72303539, compound

Product 1

HCID 68448735HCID 68448735, compoundYield 56.5%

Procedure

To 410 mg of tert-butyl{2-[3-(2,4-dichlorophenyl)-1-oxo-4-[(2-phenylethyl)carbamoyl]-3,4-dihydroisoquinolin-2(1H)-yl]ethyl}carbamate was added 4 ml of a 4 M hydrogen chloride/ethyl acetate solution, followed by stirring at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and chloroform and a 1 M aqueous sodium hydroxide solution were then added to carry out a liquid separation operation. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then evaporated under reduced pressure. The obtained residue was recrystallized from ethyl acetate-hexane to obtain 192 mg of 2-(2-aminoethyl)-3-(2,4-dichlorophenyl)-1-oxo-N-(2-phenylethyl)-1,2,3,4-tetrahydroisoquinoline-4-carboxamide as a colorless powdered crystal.

Workup

  1. customThe solvent was evaporated under reduced pressure, and chloroform
  2. additiona 1 M aqueous sodium hydroxide solution were then added
  3. customa liquid separation operation
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe obtained residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-740d88c03926413e85b087db5a93b016
Source dataset
uspto-grants-2013_07
Patent number
US08486970B2

Reaction notes

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