Chloroacetyl chloride → HCID 59396500, compound

HRID 2383052Notes

Reaction equation

HRID 2383052 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][O:7][C:8]1[C:17]([O:18][CH3:19])=[C:16]2[C:11]([CH2:12][CH2:13][NH:14][CH:15]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:10][CH:9]=1.C(=O)([O-])O.[Na+]>CCOC(C)=O>[Cl:1][CH2:2][C:3]([N:14]1[CH2:13][CH2:12][C:11]2[C:16](=[C:17]([O:18][CH3:19])[C:8]([O:7][CH3:6])=[CH:9][CH:10]=2)[CH:15]1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 67538521HCID 67538521, compound

Product 1

HCID 59396500HCID 59396500, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of chloroacetyl chloride (177 mg) in EtOAc (12 mL) was added dropwise to a mixture of 7,8-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline (350 mg), a saturated aqueous sodium hydrogen carbonate solution (50 mL), and EtOAc (50 mL) under stirring. After the dropwise addition was complete, the mixture was stirred for 2 hours and extracted with EtOAc. The extract was washed sequentially with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform-EtOH) to obtain 2-(chloroacetyl)-7,8-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline (349 mg).

Workup

  1. additionAfter the dropwise addition
  2. extractionextracted with EtOAc
  3. washThe extract was washed sequentially with a saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (chloroform-EtOH)

Sources & evidence

ORD record
ord-70a67b56e5e1446da49b54c91fb04042
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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