Tetrahydrofuran → 2-(2-Chloroethoxy)-4-(4-methylpiperazin-1-yl)-6-(naphthalene-1-sulfonylmethyl)phenylamine

HRID 2219011Notes

Reaction equation

HRID 2219011 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([N:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)[CH:8]=[C:9]([CH2:14][S:15]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:10]=1[N+:11]([O-])=O.C1COCC1>[Pd].CO>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([N:28]2[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]2)[CH:8]=[C:9]([CH2:14][S:15]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:10]=1[NH2:11]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 598427971-[3-(2-Chloroethoxy)-5-(naphthalene-1-sulfonylmethyl)-4-nitrophenyl]-4-methylpiperazine

Product 1

HCID 598427982-(2-Chloroethoxy)-4-(4-methylpiperazin-1-yl)-6-(naphthalene-1-sulfonylmethyl)phenylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-[3-(2-chloroethoxy)-5-(naphthalene-1-sulfonylmethyl)-4-nitrophenyl]-4-methylpiperazine (0.45 g, 0.85 mmoles) and 10% Pd/C in a 1:1 mixture of THF and methanol was hydrogenated on a Parr hydrogenator at 40 lb/in2 for 20 hours. The reaction mixture was filtered through Celite. The filtrate was diluted with EtOAc, washed with water, dried over Na2SO4, and concentrated under vacuum to afford the title compound as an off white solid (0.4 g, 0.82 mmoles), identified by HNMR and mass spectral analyses.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. additionThe filtrate was diluted with EtOAc
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b0f5c5bfda234b9e86780698ad0f6bc2
Source dataset
uspto-grants-2008_08
Patent number
US07414051B2

Reaction notes

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