1-(4-nitro 2-(2-((tetrahydro-2H-pyran 2-yl)oxy)ethoxy)phenyl)-4-(oxetan-3-yl)piperazine → 4-(4-(oxetan-3-yl)piperazin-1-yl)-3-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)aniline

HRID 928691Notes

Reaction equation

HRID 928691 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH:16]3[CH2:19][O:18][CH2:17]3)[CH2:12][CH2:11]2)=[C:6]([O:20][CH2:21][CH2:22][O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH:5]=1)([O-])=O>C(O)C.[Pd]>[O:18]1[CH2:17][CH:16]([N:13]2[CH2:14][CH2:15][N:10]([C:7]3[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][C:6]=3[O:20][CH2:21][CH2:22][O:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)[CH2:11][CH2:12]2)[CH2:19]1

Participants

4

Reactant 1

HCID 1181879201-(4-nitro 2-(2-((tetrahydro-2H-pyran 2-yl)oxy)ethoxy)phenyl)-4-(oxetan-3-yl)piperazine

Product 1

HCID 1181879194-(4-(oxetan-3-yl)piperazin-1-yl)-3-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 1-(4-nitro-2-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)phenyl)-4-(oxetan-3-yl)piperazine XXIII (2100 mg, 5.1 mmol) in ethanol (50 mL) was added 10% Pd/C (50% wet, 390 mg dry weight) in a 500-mL Parr hydrogenation bottle. The bottle was evacuated, charged with hydrogen gas to a pressure of 50 psi and shaken at rt for 2 h on a Parr hydrogenation apparatus. The reaction mixture was filtered, and washed with ethanol. The filtrate was concentrated in vacuo to give 4-(4-(oxetan-3-yl)piperazin-1-yl)-3-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)aniline XXIV.

Workup

  1. customThe bottle was evacuated
  2. additioncharged with hydrogen gas to a pressure of 50 psi
  3. filtrationThe reaction mixture was filtered
  4. washwashed with ethanol
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-678eea1903884b3fa703a905d3f871df
Source dataset
uspto-grants-2016_03
Patent number
US09290505B2

Reaction notes

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