2-Benzyl-6-nitro-1,2,3,4-tetrahydroisoquinoline → HCID 15489611, compound

HRID 1954427Notes

Reaction equation

HRID 1954427 reaction equation
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:18]([O-])=O)[CH:14]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pt]=O.C1COCC1>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH2:18])[CH:14]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 222696172-Benzyl-6-nitro-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 15489611HCID 15489611, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A THF (184 mL) solution of compound (17) (4.6 g, 17 mmole) with platinum oxide (230 mg) was hydrogenated for 18 hrs. at 50 psi. The catalyst was filtered off and platinum oxide (230 mg) was added and the hydrogenation continued for 72 hrs. The completed hydrogenation was filtered to provide a THF solution of the intermediate, 2-benzyl-1,2,3,4-tetrahydroisoquinolin-6-yl amine (18). Triethylamine was added to the THF solution of (18) followed by the dropwise addition of 4'-trifluoromethylbiphenyl-2-carbonyl chloride (4.88 g., 17 mmole) from Example 3. The contents were stirred subsequently for 17 hrs. The solvent was removed under vacuum, water (50 mL) was added, the contents stirred for 3 hr., the product filtered off and dried under vacuum to yield 5.93 g (71%) of compound (19) as a white solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. additionplatinum oxide (230 mg) was added
  3. filtrationThe completed hydrogenation was filtered

Sources & evidence

ORD record
ord-a82d10fc0fed40eb9e7a198e9517fc83
Source dataset
uspto-grants-2000_09
Patent number
US06121283

Reaction notes

Loading…