1,2,3,4-Tetrahydroisoquinoline → HCID 20556841, compound

HRID 1660504Notes

Reaction equation

HRID 1660504 reaction equation
[C:1]1([C:7]2[NH:12][CH2:11][CH:10](COS(C3C=CC(C)=CC=3)(=O)=O)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27][NH:26]1.[C:35](=O)([O-])[O-].[K+].[K+]>ClC1C=CC=CC=1>[C:1]1([C:7]2[N:12]([CH3:35])[CH2:11][CH:10]([N:26]3[CH2:27][CH2:28][C:29]4[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:25]3)[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 11430Potassium CarbonateHCID 178427692HCID 178427692, compound

Product 1

HCID 20556841HCID 20556841, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To 3.46 g. of 3-phenyl-6-tosyloxymethyl-5,6-dihydro-4H-1,2,4-oxadiazine 1.33 g. of 1,2,3,4-tetrahydro-isoquinoline, 1.38 g. of anhydrous potassium carbonate and 30 ml. of chlorobenzene are added. The reaction mixture is refluxed for 2 hours, whereupon it is decolored and filtered while hot. Upon cooling 1.95 g. of 3-phenyl-6-(1,2,3,4-tetrahydro-2-isoquinolyl)-methyl-5,6-dihydro-4H-1,2,4-oxadiazine are obtained in crystalline form. The product has the same properties as the product of Example 4. Melting point: 187° to 189° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 2 hours, whereupon it
  2. filtrationfiltered while hot
  3. temperatureUpon cooling 1.95 g

Sources & evidence

ORD record
ord-9a955a4bd83b44efb897739ca24bd4f2
Source dataset
uspto-grants-1981_12
Patent number
US04308270

Reaction notes

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