Acetyl chloride → 1-[2-(Trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-7-yl]ethanone

HRID 2375354Notes

Reaction equation

HRID 2375354 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].[Cl-].[Cl-].[Cl-].[Al+3].[C:21](Cl)(=[O:23])[CH3:22]>C(=S)=S>[F:16][C:2]([F:1])([F:15])[C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([C:21](=[O:23])[CH3:22])=[CH:10][CH:11]=2)[CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6152162-(Trifluoroacetyl)-1,2,3,4-tetrahydroisoquinolineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 128231911-[2-(Trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-7-yl]ethanoneYield 57.9%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

2-(Trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline (140 mmol, 32.00 g) was introduced into CS2 (190 ml). Aluminum trichloride (837 mmol, 111.60 g) was added thereto in portions at room temperature. Acetyl chloride (419.12 mmol, 32.90 g) was then added dropwise in such a way that gentle refluxing took place, and the mixture was heated to reflux for a further hour. The reaction mixture was poured into ice-water and extracted with dichloromethane. The organic phase was dried, filtered with suction and concentrated and then stirred with isopropanol. 22 g of the title compound were obtained with a melting point of 80° C.

Workup

  1. customat room temperature
  2. temperaturethat gentle refluxing
  3. temperaturethe mixture was heated
  4. temperatureto reflux for a further hour
  5. extractionextracted with dichloromethane
  6. customThe organic phase was dried
  7. filtrationfiltered with suction
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e81a8e3da66443f2a55c59262c3a66cb
Source dataset
uspto-grants-2008_12
Patent number
US07465744B2

Reaction notes

Loading…