Hydrochloric Acid → HCID 66868651, compound

HRID 1850821Notes

Reaction equation

HRID 1850821 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH2:24][CH2:25][NH:26]C(=O)OC(C)(C)C)[CH:21]=4)[CH2:16][CH2:15][N:14]=3)[CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1>ClCCl>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH2:24][CH2:25][NH2:26])[CH:21]=4)[CH2:16][CH2:15][N:14]=3)[CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66868974HCID 66868974, compound

Product 1

HCID 66868651HCID 66868651, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After adding HCl dissolved in isopropanole (15 ml, 6 molar solution) to a solution of tert-butyl 2-(1-(1-(4-chlorophenyl)cyclobutyl)-3,4-dihydroisoquinolin-7-yloxy)ethylcarbamate (6.20 g, 13.6 mmol) in dichloromethane (200 ml) the mixture was stirred for 14 h. The resulting precipitate was removed by filtration and washed with diisopropylether. After drying the filtrate was dissolved in water and basified with 2N NaOH. Extraction with dichloromethane the combined organic layers were washed with water and saturated NaCl solution. Drying with MgSO4 and removal of the solvent gave 2-(1-(1-(4-chlorophenyl)cyclobutyl)-3,4-dihydroisoquinolin-7-yloxy)ethanamine (3.77 g, 10.6 mmol, 78%).

Workup

  1. customThe resulting precipitate was removed by filtration
  2. washwashed with diisopropylether
  3. customAfter drying the filtrate
  4. dissolutionwas dissolved in water and basified with 2N NaOH
  5. extractionExtraction with dichloromethane the combined organic layers
  6. washwere washed with water and saturated NaCl solution
  7. dry with materialDrying with MgSO4 and removal of the solvent

Sources & evidence

ORD record
ord-068d04d8a1f849d4966f4deb02e33a9e
Source dataset
uspto-grants-2015_02
Patent number
US08957089B2

Reaction notes

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