1,2,3,4-Tetrahydroisoquinoline → HCID 59868717, compound

HRID 383716Notes

Reaction equation

HRID 383716 reaction equation
[N:1]12[CH2:11][CH2:10][CH2:9]N=[C:7]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2.Cl[C:13]1[N:18]=[C:17]([CH3:19])[C:16]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:15]([CH3:25])[N:14]=1.C1C2C(=CC=CC=2)CCN1>CS(C)=O>[CH2:11]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:9]=2)[CH2:6][CH2:7][N:1]1[C:13]1[N:18]=[C:17]([CH3:19])[C:16]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:15]([CH3:25])[N:14]=1

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59868739HCID 59868739, compound

Product 1

HCID 59868717HCID 59868717, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1,8-diazabicyclo[5.4.0]undec-7-ene (1.086 g, 7.15 mmol) was added to a mixture of 6b (1.02 g, 4.75 mmol) and 1,2,3,4-tetrahydroisoquinoline (0.95 g, 7.13 mmol) in DMSO (5 ml) at 0° C. over 5 minutes. The mixture was stirred for an additional 5 minutes at room temperature. The mixture was washed with brine, extracted with ethyl acetate and chromatographed to yield 6c (1.43 g, 4.5 mmol, 95%).

Workup

  1. washThe mixture was washed with brine
  2. extractionextracted with ethyl acetate
  3. customchromatographed

Sources & evidence

ORD record
ord-c776c9e311144139b2075d23e7c1bb21
Source dataset
uspto-grants-2013_02
Patent number
US08367684B2

Reaction notes

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