Chloroacetyl chloride → HCID 59396492, compound

HRID 2383021Notes

Reaction equation

HRID 2383021 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[C:6]1([C:12]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[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.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[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:12]1([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 521998p-Toluenesulfonic acid monohydrateHCID 59396601HCID 59396601, compound

Product 1

HCID 59396492HCID 59396492, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Chloroacetyl chloride (0.151 mL) was added to a solution of 1,1-diphenyl-1,2,3,4-tetrahydroisoquinoline (339 mg) and p-toluenesulfonate monohydrate (11.3 mg) in toluene (5 mL). The mixture was heated under reflux for 3 hours. The solvent was evaporated under reduced pressure, and EtOAc and an aqueous 1 M HCl solution were added to the residue. The organic layer was washed with water, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain 2-(chloroacetyl)-1,1-diphenyl-1,2,3,4-tetrahydroisoquinoline (452 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customThe solvent was evaporated under reduced pressure, and EtOAc
  4. additionan aqueous 1 M HCl solution were added to the residue
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and saturated brine, dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ef722d5a99f54f4691ed642429c6ca81
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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