Dichloromethane → Ethyl 1-phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylate

HRID 850360

Reaction equation

HRID 850360 reaction equation
ClCCl.[C:4]1([CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][NH:11]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(N(CC)CC)C>[C:4]1([CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][N:11]2[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 10928Ethyl chloroformateHCID 1001371,2,3,4-Tetrahydro-1-phenylisoquinoline

Product 1

HCID 10423841Ethyl 1-phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a 130 ml dichloromethane solution containing 6.28 g of 1-phenyl-1,2,3,4-tetrahydroisoquinoline and 3.34 g of triethylamine, 3.1 ml of ethyl chloroformate was added dropwise under ice-cooling, followed by stirring at room temperature overnight. The reaction solution was washed successively with water, 1N hydrochloric acid, water and brine and then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, thereby 10.58 g of ethyl 1-phenyl-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate was obtained as pale yellow oil.

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling
  3. washThe reaction solution was washed successively with water, 1N hydrochloric acid, water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d34a8cf1bdd142488f513847084b3196
Source dataset
uspto-grants-2000_01
Patent number
US06017927

Linked notes

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