Hydrochloric Acid → 2-({1-[1-(4-Fluorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-yl}oxy)ethanamine

HRID 242060Notes

Reaction equation

HRID 242060 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][NH:25]C(=O)OC(C)(C)C)[CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl>ClCCl.C(O)(C)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][NH2:25])[CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 70258703tert-Butyl[2-({1-[1-(4-fluorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-yl}oxy)ethyl]carbamate

Product 1

HCID 582463242-({1-[1-(4-Fluorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-yl}oxy)ethanamine

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl [2-({1-[1-(4-fluorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-yl}oxy)ethyl]carbamate (2.5 g, 5.7 mmol) was dissolved in dichloromethane (30 mL) and 5N hydrochloric acid in isopropanol (20 mL) was added. After stirring over night at room temperature the solvent was evaporated in vacuo. Water (30 mL) was added and the aqueous phase was neutralized with saturated aqueous NaHCO3 and extracted with dichloromethane. The combined organic layers were washed with brine (20 mL), dried (MgSO4) and concentrated in vacuo. The crude product (1.76 g) was used without purification for the next step.

Workup

  1. customwas evaporated in vacuo
  2. additionWater (30 mL) was added
  3. extractionextracted with dichloromethane
  4. washThe combined organic layers were washed with brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude product (1.76 g) was used without purification for the next step

Sources & evidence

ORD record
ord-1087c3436a044653910333ebe735c45e
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

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