HCID 67536962, compound → HCID 59396601, compound

HRID 2383022Notes

Reaction equation

HRID 2383022 reaction equation
C([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)C1C=CC=CC=1>[Pd].C1COCC1.CO>[C:24]1([C:9]2([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:16][CH2:17][NH:8]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 1

HCID 67536962HCID 67536962, compound

Product 1

HCID 59396601HCID 59396601, compoundYield 24.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

10% Pd-supported carbon (900 mg) was added to a solution of 2-benzyl-1,1-diphenyl-1,2,3,4-tetrahydroisoquinoline (1.81 g) in a 2:1 THF-MeOH mixture (30 mL). The mixture was stirred under a hydrogen atmosphere at room temperature for 16 hours. Further, 10% Pd-supported carbon (900 mg) was added to the mixture, followed by stirring for 8 hours. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-EtOAc) to obtain 1,1-diphenyl-1,2,3,4-tetrahydroisoquinoline (339 mg).

Workup

  1. stirringby stirring for 8 hours
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane-EtOAc)

Sources & evidence

ORD record
ord-bd55f40d131245aabe909c7cebffd17f
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

Loading…