Ethanol → HCID 118185277, compound

HRID 928695Notes

Reaction equation

HRID 928695 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH:17]3[CH2:20][O:19][CH2:18]3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.C(O)C.[Cl-].[NH4+]>[Fe].O>[O:19]1[CH2:20][CH:17]([CH2:16][N:13]2[CH2:14][CH2:15][N:10]([C:7]3[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=3)[CH2:11][CH2:12]2)[CH2:18]1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 118185280HCID 118185280, compound

Product 1

HCID 118185277HCID 118185277, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a round-bottomed flask equipped with a stirring bar, were added 1-(4-nitrophenyl)-4-(oxetan-3-ylmethyl)piperazine XXIX (3.20 g, 11.54 mmol), ethanol (60 mL) and water (60 mL). Following the addition of iron (4.51 g, 80.77 mmol) and ammonium chloride (4.32 g, 80.77 mmol), the reaction mixture was heated at 80° C. for 1 h, then filtered through Celite and washed with DCM (5 mL×5). The resulting filtrate was extracted with DCM (20 mL×3). The combined organic extracts were washed with water (20 mL×2), brine (20 mL×1), dried over Na2SO4, and concentrated in vacuo. The desired 4-(4-(oxetan-3-ylmethyl)piperazin-1-yl)aniline XXX was obtained.

Workup

  1. customTo a round-bottomed flask equipped with a stirring bar
  2. filtrationfiltered through Celite
  3. washwashed with DCM (5 mL×5)
  4. extractionThe resulting filtrate was extracted with DCM (20 mL×3)
  5. washThe combined organic extracts were washed with water (20 mL×2), brine (20 mL×1)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf190851a8df4de491fe67175a641c7f
Source dataset
uspto-grants-2016_03
Patent number
US09290505B2

Reaction notes

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