HCID 59807091, compound → HCID 59807148, compound

HRID 1922518Notes

Reaction equation

HRID 1922518 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[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[CH2:9][CH2:8][CH2:7]2)([O-])=O>C(O)C.O1CCCC1.[Pd]>[O:20]1[CH2:21][CH2:22][N:17]([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)[CH2:18][CH2:19]1

Participants

5

Reactant 1

HCID 59807091HCID 59807091, compound

Product 1

HCID 59807148HCID 59807148, compoundYield 84.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-(3-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)propyl)morpholine (250 mg, 0.819 mmol) in Ethanol (4 ml) and Tetrahydrofuran (4.00 ml) was added Palladium on activated carbon, 10 wt. % (87 mg, 0.082 mmol). The reaction was then stirred under a hydrogen atmosphere (balloon pressure) for 2 h. When TLC analysis showed that the starting material was consumed, the mixture was filtered through a pad of celite which was then washed with methanol. The filtrate was concentrated, giving the desired 1-(3-morpholinopropyl)-1,2,3,4-tetrahydroquinolin-6-amine (190 mg, 0.690 mmol, 84% yield) as a dark oil.

Workup

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

Sources & evidence

ORD record
ord-613cd192cc7248ffb3d74889a18ed6bd
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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