Sodium Bicarbonate → 6,7-Dichloro-1,2,3,4-tetrahydroisoquinoline

HRID 420796Notes

Reaction equation

HRID 420796 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[Cl:13])[CH2:9][NH:8][CH2:7][CH2:6]2.C([O-])(O)=O.[Na+]>O.C(Cl)Cl>[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[Cl:13])[CH2:9][NH:8][CH2:7][CH2:6]2

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 12595078HCID 12595078, compound

Product 1

HCID 125950776,7-Dichloro-1,2,3,4-tetrahydroisoquinolineYield 100.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

6,7-dichloro-1,2,3,4-tetrahydroisoquinoline HCl salt (550 mg, 2.31 mmol) was dissolved in water (5 mL) and DCM (20 mL). Aqueous saturated NaHCO3 (10 mL) was added and the organic phase was separated. The aqueous phase was extracted twice with DCM (20 mL), the organic phases were combined, dried (Na2SO4), and filtered to give 6,7-dichloro-1,2,3,4-tetrahydro-isoquinoline (470 mg, quant.).

Workup

  1. customthe organic phase was separated
  2. extractionThe aqueous phase was extracted twice with DCM (20 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-2d46b5ffb69548b0a33cbe121da15847
Source dataset
uspto-grants-2012_01
Patent number
US08097636B2

Reaction notes

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