Chloroacetyl chloride → HCID 59396660, compound

HRID 2383012Notes

Reaction equation

HRID 2383012 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[C:6]1([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14][NH:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])O.[Na+]>CCOC(C)=O.O>[Cl:1][CH2:2][C:3]([N:13]1[CH2:14][CH2:15][C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@@H:12]1[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:4]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 1382087(1S)-1,2,3,4-Tetrahydro-1-phenylisoquinoline

Product 1

HCID 59396660HCID 59396660, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of chloroacetyl chloride (1.03 g) and EtOAc (5 mL) was added dropwise with stirring to a mixture of (1S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (1.58 g), sodium hydrogen carbonate (960 mg), water (25 mL) and EtOAc (25 mL), followed by stirring at room temperature for 2 hours. The reaction liquid was extracted with EtOAc, and the extract was washed sequentially with saturated aqueous sodium bicarbonate and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-AcOEt, 4:1) to obtain (1S)-2-(chloroacetyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (2.14 g).

Workup

  1. additionwas added dropwise
  2. customThe reaction liquid
  3. extractionwas extracted with EtOAc
  4. washthe extract was washed sequentially with saturated aqueous sodium bicarbonate and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane-AcOEt, 4:1)

Sources & evidence

ORD record
ord-adc9bc70c9b2402894a13c7ca290d6e6
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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