Triethylamine → Carbamic acid, [2-(3-isoquinolinyl)ethyl]-, ethyl ester

HRID 1181435Notes

Reaction equation

HRID 1181435 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:5]=[CH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2.C(N(CC)CC)C.Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>ClCCl>[CH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[C:4]([CH2:3][CH2:2][NH:1][C:22](=[O:23])[O:24][CH2:25][CH3:26])[N:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 69523043HCID 69523043, compound

Product 1

HCID 69522231Carbamic acid, [2-(3-isoquinolinyl)ethyl]-, ethyl esterYield 59.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-bath cooled solution of 3-(2-aminoethyl)isoquinoline (Description 113; 2.70 g, 15.7 mmol) and triethylarnine (2.84 ml, 20.41 mmol) in anhydrous dichloromethane (75 ml) was added slowly ethyl chloroformate (1.65 ml, 17.27 mmol) and the resulting mixture stirred at room temperature for 1 hour. The mixture was washed with water, sat NaCl, dried over Na2SO4, filtered and evaporated. The residue was purified by column chromatography on silica elution with a gradient rising from DCM to 2% MeOH in DCM+0.5% NH4OH to give the title compound (2.27 g, 59%).

Workup

  1. washThe mixture was washed with water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica elution with a gradient

Sources & evidence

ORD record
ord-c1530443f6eb44f1895f6f8e964a752b
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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