4-[2-(4-Nitro-phenyl)-ethanesulfonyl]-morpholine → 4-[2-(Morpholine-4-sulfonyl)-ethyl]-phenylamine

HRID 1508061Notes

Reaction equation

HRID 1508061 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][S:12]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)(=[O:14])=[O:13])=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[N:15]1([S:12]([CH2:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)(=[O:14])=[O:13])[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1

Participants

4

Reactant 1

HCID 589943904-[2-(4-Nitro-phenyl)-ethanesulfonyl]-morpholine

Product 1

HCID 589945154-[2-(Morpholine-4-sulfonyl)-ethyl]-phenylamineYield 34.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 370 mg (1.11 mmol) of 4-[2-(4-nitro-phenyl)-ethanesulfonyl]-morpholine (as prepared in the previous step) in MeOH (20 mL) was treated with 10% Pd/C (Degussa type E101-NE/W, Aldrich, 50% by weight water) and H2 (1 atm) at RT for 3 h. The mixture was filtered through Celite, the filter cake was washed with MeOH, and solvents were evaporated in vacuo. Silica gel chromatography of the residue on a 50-g Varian MegaBond Elut SPE column with 50-70% EtOAc-hexane afforded 103 mg (34%) of the title compound as an off-white solid: Mass spectrum (ESI, m/z): Calcd. for C12H18N2O3S, 271.1 (M+H). found 270.9.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe filter cake was washed with MeOH, and solvents
  3. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-482ea6b89ea041ef9bedfab9df226588
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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