6-Nitro-1-(3-(pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinoline → 1-(3-(Pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinolin-6-amine

HRID 1922526Notes

Reaction equation

HRID 1922526 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)[CH2:9][CH2:8][CH2:7]2)([O-])=O>C(O)C.O1CCCC1.[Pd]>[N:17]1([CH2:16][CH2:15][CH2:14][N:10]2[C:11]3[C:6](=[CH:5][C:4]([NH2:1])=[CH:13][CH:12]=3)[CH2:7][CH2:8][CH2:9]2)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 1

HCID 533923476-Nitro-1-(3-(pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinoline

Product 1

HCID 533923491-(3-(Pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinolin-6-amineYield 98.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6-nitro-1-(3-(pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinoline (270 mg, 0.933 mmol) in ethanol (5 ml) and tetrahydrofuran (5.00 ml) was added palladium on activated carbon, 10 wt. % (99 mg, 0.093 mmol). The resulting suspension was stirred under an atmosphere of hydrogen (balloon pressure) and monitored by TLC. After 2 h, the reaction mixture was filtered through a pad of celite, which was then washed with methanol. The filtrate was then concentrated, giving the desired 1-(3-(pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinolin-6-amine (238 mg, 0.918 mmol, 98% yield) as a dark oil.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of celite, which
  2. washwas then washed with methanol
  3. concentrationThe filtrate was then concentrated

Sources & evidence

ORD record
ord-addd9cec309648b1a24e89ca9576a527
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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