Morpholin-4-yl-(4-{[(7-nitro-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-methyl}-piperidin-1-yl)-methanone → (4-{[(7-Amino-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-methyl)-piperidin-1-yl)-morpholin-4-yl-methanone

HRID 983472Notes

Reaction equation

HRID 983472 reaction equation
[N:1]1([C:7]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][N:16]([CH:20]3[CH2:29][CH2:28][C:27]4[C:22](=[CH:23][C:24]([N+:30]([O-])=O)=[CH:25][CH:26]=4)[CH2:21]3)[CH2:17][CH2:18][CH3:19])[CH2:11][CH2:10]2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H][H]>C(O)C.[Pd]>[NH2:30][C:24]1[CH:23]=[C:22]2[C:27]([CH2:28][CH2:29][CH:20]([N:16]([CH2:15][CH:12]3[CH2:11][CH2:10][N:9]([C:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[O:8])[CH2:14][CH2:13]3)[CH2:17][CH2:18][CH3:19])[CH2:21]2)=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 22560631Morpholin-4-yl-(4-{[(7-nitro-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-methyl}-piperidin-1-yl)-methanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 22560664(4-{[(7-Amino-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-methyl)-piperidin-1-yl)-morpholin-4-yl-methanoneYield 86.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of morpholin-4-yl-(4-{[(7-nitro-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-methyl}-piperidin-1-yl)-methanone (540 mg, 1.2 mmol) in ethanol (30 mL) was added 10% palladium on charcoal (50 mg). The solution was shaken on a Parr shaker for 24 h at 55 psi of hydrogen. The solution was filtered through Celite® and concentrated to afford (4-{[(7-amino-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-methyl}-piperidin-1-yl)-morpholin-4-yl-methanone (432 mg) 95, [M+H]+=415; which was used directly.

Workup

  1. filtrationThe solution was filtered through Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-dec849f15eba4996b975e5ba3fc85db3
Source dataset
uspto-grants-2005_03
Patent number
US06864266B2

Reaction notes

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