Hydrogen chloride-ethyl acetate → HCID 68448735, compound

HRID 1747072Notes

Reaction equation

HRID 1747072 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH:18]([C:19](=[O:29])[NH:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:30])[N:10]1[CH2:31][CH2:32][NH:33]C(=O)OC(C)(C)C.Cl.C(OCC)(=O)C>>[NH2:33][CH2:32][CH2:31][N:10]1[CH:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[CH:18]([C:19]([NH:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:29])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:30]

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-26c2e910ce2f4b9d81f73e57c9ec302d
Source dataset
uspto-grants-2015_10
Patent number
US09150541B2

Reaction notes

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