Chloroacetyl chloride → HCID 21491380, compound

HRID 1942243Notes

Reaction equation

HRID 1942243 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][CH2:9][CH2:8][CH2:7]2.[Cl:12][CH2:13][C:14](Cl)=[O:15].C(N(CC)CC)C>C(Cl)Cl>[Cl:12][CH2:13][C:14]([N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[CH3:1])[CH2:7][CH2:8][CH2:9]1)=[O:15]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 27741668-Methyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 21491380HCID 21491380, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 8-methyl-1,2,3,4-tetrahydroquinolin (1) (8.0 g, 54.3 mmol) in dry CH2Cl2 (250 mL) at 0° C. was added chloroacetyl chloride (4.8 mL, 60.3 mmol) followed by addition of triethylamine (8.4 mL, 60.3 mmol). The reaction mixture was stirred overnight under N2 and then diluted with CH2Cl2 (300 mL), washed with 1M HCl (2×225 mL), H2O (2×250 mL) and brine. Dried over Na2SO4, filtered and concentrated under reduce pressure to 12.67 g of crude material which was purified by column chromatography (EtOAc/Hexanes). Obtained 11.76 g (52.6 mmol) of target 2 (off-white solid) in 97% yield.

Workup

  1. washwashed with 1M HCl (2×225 mL), H2O (2×250 mL) and brine
  2. dry with materialDried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customwas purified by column chromatography (EtOAc/Hexanes)
  6. customObtained 11.76 g (52.6 mmol) of target 2 (off-white solid) in 97% yield

Sources & evidence

ORD record
ord-6546a4e336204908b054a6a66884c316
Source dataset
uspto-grants-2013_03
Patent number
US08389546B2

Reaction notes

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