8-(1-tert-butyl-1,2,3,6-tetrahydropyridin-4-yl)-6-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2H-quinolizin-2-one hydrochloride → 8-(1-tert-butylpiperidin-4-yl)-6-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2H-quinolizin-2-one

HRID 1360677Notes

Reaction equation

HRID 1360677 reaction equation
Cl.[C:2]([N:6]1[CH2:11][CH:10]=[C:9]([C:12]2[CH:13]=[C:14]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[Cl:37])[N:15]3[C:20]([CH:21]=2)=[C:19]([C:22]2[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:29])[C:18](=[O:30])[CH:17]=[CH:16]3)[CH2:8][CH2:7]1)([CH3:5])([CH3:4])[CH3:3]>CO.C(OCC)(=O)C.[Pt]=O>[C:2]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:13]=[C:14]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[Cl:37])[N:15]3[C:20]([CH:21]=2)=[C:19]([C:22]2[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:29])[C:18](=[O:30])[CH:17]=[CH:16]3)[CH2:8][CH2:7]1)([CH3:5])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 160646028-(1-tert-butyl-1,2,3,6-tetrahydropyridin-4-yl)-6-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2H-quinolizin-2-one hydrochloride

Product 1

HCID 160646048-(1-tert-butylpiperidin-4-yl)-6-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2H-quinolizin-2-one

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution of 8-(1-tert-butyl-1,2,3,6-tetrahydropyridin-4-yl)-6-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2H-quinolizin-2-one hydrochloride (Example 19, 24 mg) in methanol/ethyl acetate=1/5 was added platinum oxide (9 mg). The solution was hydrogenated under hydrogen (1 atm) for 1 h. The mixture was filtered though celite and concentrated. The residue was purified by silica gel (methylene chloride/methanol/2N ammonia=10/1/0.2) to give the title compound.

Workup

  1. filtrationThe mixture was filtered though celite and
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel (methylene chloride/methanol/2N ammonia=10/1/0.2)

Sources & evidence

ORD record
ord-4dd558562d2d4992965cd65f1b1dfbc2
Source dataset
uspto-grants-2011_02
Patent number
US07879875B2

Reaction notes

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