Chloroacetyl chloride → HCID 67537379, compound

HRID 2383038Notes

Reaction equation

HRID 2383038 reaction equation
[C:1]([O:7][C:8]([CH3:20])([CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][NH:11]1)[CH3:9])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Cl:21][CH2:22][C:23](Cl)=[O:24]>CCOC(C)=O>[C:1]([O:7][C:8]([CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][N:11]1[C:23](=[O:24])[CH2:22][Cl:21])([CH3:20])[CH3:9])(=[O:6])[C:2]([CH3:5])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 67537497HCID 67537497, compound

Product 1

HCID 67537379HCID 67537379, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

1-methyl-1-(1,2,3,4-tetrahydroisoquinolin-1-yl)ethyl pivalate (2.79 g) was dissolved in a 1:4 mixed solvent (30 mL) of EtOAc-saturated aqueous sodium bicarbonate. A solution of chloroacetyl chloride (0.9 mL) in EtOAc (6 mL) was added dropwise to the reaction liquid under ice-cooling, followed by stirring at room temperature for 2 hours and extraction with EtOAc. The extract was washed with saturated brine, and then dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (hexane-EtOAc) to obtain 1-[2 (chloroacetyl)-1,2,3,4-tetrahydroisoquinolin-1-yl]-1-methylethyl pivalate (3.01 g).

Workup

  1. temperaturecooling
  2. extractionextraction with EtOAc
  3. washThe extract was washed with saturated brine
  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-5a86e1356e3e4a10a61e95216e9fbff3
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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