HCID 7122702, compound → HCID 58452964, compound

HRID 1876830Notes

Reaction equation

HRID 1876830 reaction equation
[CH3:1][C@:2]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:11]2[C:6]3=[C:7]([C@:15]([CH3:24])([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:16][CH2:17][N:5]3[CH2:4][CH2:3]1)[CH:8]=[C:9]([N+:12]([O-])=O)[CH:10]=2>C1COCC1.[Pd]>[CH3:1][C@:2]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:11]2[C:6]3=[C:7]([C@:15]([CH3:24])([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:16][CH2:17][N:5]3[CH2:4][CH2:3]1)[CH:8]=[C:9]([NH2:12])[CH:10]=2

Participants

4

Reactant 1

HCID 7122702HCID 7122702, compound

Product 1

HCID 58452964HCID 58452964, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (1S,7S)-1,7-dimethyl-9-nitro-1,7-diphenyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinoline (7), (2 g, 5 mmol), in THF (60 mL) was subjected to hydrogenation reaction by the action of 10% Pd/C (200 mg) under H2 balloon at room temperature for 12 h. The mixture was filtered through Celite and freed of solvent under reduced pressure to get (1S,7S)-1,7-dimethyl-1,7-diphenyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-amine (9) as a solid, (1.5 g, 100%) on the basis of recovered starting material (7), (390 mg).

Workup

  1. filtrationThe mixture was filtered through Celite

Sources & evidence

ORD record
ord-28116b8f214649b9ab8ae4f7dfa8ebe6
Source dataset
uspto-grants-2012_11
Patent number
US08309729B2

Reaction notes

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