1,2,3,4-Tetrahydroisoquinoline → 3-Chloro-1-(3,4-dihydroisoquinolin-2(1H)-yl)propan-1-one

HRID 1178233Notes

Reaction equation

HRID 1178233 reaction equation
[Cl:1][CH2:2][CH2:3][C:4](Cl)=[O:5].[CH2:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][NH:8]1>O1CCCC1>[Cl:1][CH2:2][CH2:3][C:4]([N:8]1[CH2:9][CH2:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1)=[O:5]

Participants

4

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 693643-Chloropropionyl chloride

Product 1

HCID 2464273-Chloro-1-(3,4-dihydroisoquinolin-2(1H)-yl)propan-1-oneYield 59.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

A solution of 3-chloropropanoyl chloride (10.5 g) in tetrahydrofuran (400 mL) was cooled down to 6° C. followed by the addition of a solution of 3,4-dihydro-1H-isoquinoline (10.0 g). The resulting mixture was stirred at 10° C. for 30 min, filtered and concentrated in vacuo. The residue was subjected to a standard aqueous work up procedure followed by purification by flash chromatography on silicagel (eluent: ethyl acetate/heptane 1:1) to give the product as a colourless oil (10 g).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customfollowed by purification by flash chromatography on silicagel (eluent: ethyl acetate/heptane 1:1)

Sources & evidence

ORD record
ord-d6f3dbe3786143bfbd2646dd1c06189e
Source dataset
uspto-grants-2007_10
Patent number
US07276508B2

Reaction notes

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