1,2,3,4-Tetrahydroisoquinoline → HCID 39866, compound

HRID 2397939Notes

Reaction equation

HRID 2397939 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:12])[CH2:7]2.C(=O)(O)[O-].[K+].[F:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22].C1C2C(=CC=CC=2)CCN1>C1C=CC=CC=1>[F:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([NH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:12])[CH2:7]2)=[O:22]

Participants

6

Reactant 4

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 98082-Fluorobenzoyl chlorideHCID 516893Potassium BicarbonateHCID 141712692-Methyl-1,2,3,4-tetrahydroisoquinolin-5-amine

Product 1

HCID 39866HCID 39866, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

5-Amino-2-methyl-1,2,3,4-tetrahydroisoquinoline (5.0 g) prepared as in Example 4 was dissolved in dry benzene (75 ml) and 0.5 g of dry potassium bicarbonate was added. A 0.1 mole excess of 2-fluorobenzoyl chloride was dissolved in dry benzene (75 ml) and this solution was added to the solution of the tetrahydroisoquinoline. A white precipitate formed immediately. The mixture was refluxed for 1 hour to insure that the reaction had gone to completion. The precipitate was collected by vacuum filtration and washed with 10% sodium carbonate solution followed by water. The washings were discarded and the remaining residue was recrystallized from ethyl acetate to yield 6.8 g of the desired product as white crystals, m.p. 112°-112.5° C.

Workup

  1. customA white precipitate formed immediately
  2. temperatureThe mixture was refluxed for 1 hour
  3. filtrationThe precipitate was collected by vacuum filtration
  4. washwashed with 10% sodium carbonate solution
  5. customthe remaining residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-476796b07cd948a5b1d8e2d0a94684b9
Source dataset
uspto-grants-1977_05
Patent number
US04022900

Reaction notes

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