Chloroacetyl chloride → HCID 59396503, compound

HRID 2383011Notes

Reaction equation

HRID 2383011 reaction equation
Cl.[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][NH:9][CH:10]2[CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+].[Cl:24][CH2:25][C:26](Cl)=[O:27]>CCOC(C)=O>[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([C:26](=[O:27])[CH2:25][Cl:24])[CH:10]2[CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 67537734HCID 67537734, compound

Product 1

HCID 59396503HCID 59396503, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

7-chloro-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline hydrochloride (899 mg) was added to saturated aqueous sodium bicarbonate (15 mL), to which EtOAc (10 mL) was then further added. A solution of chloroacetyl chloride (390 mg) in EtOAc (5 mL) was added dropwise to the reaction liquid over 5 minutes. The reaction liquid was stirred for 1 hour, extracted with EtOAc, and dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (hexane-EtOAc) to obtain 7-chloro-2-(chloroacetyl)-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline (888 mg).

Workup

  1. additionwas then further added
  2. customThe reaction liquid
  3. extractionextracted with EtOAc
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe resulting residue was purified by silica gel column chromatography (hexane-EtOAc)

Sources & evidence

ORD record
ord-901d93a993ea49cbbf9059e24a849d88
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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