HCID 22674219, compound → HCID 60108777, compound

HRID 1005664Notes

Reaction equation

HRID 1005664 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[C:12]([N+:24]([O-])=O)=[C:13]([N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)[CH:14]=[CH:15][CH:16]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O1CCCC1.[OH-].[OH-].[Pd+2]>[C:1]1([S:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)[C:12]=2[NH2:24])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 22674219HCID 22674219, compound

Product 1

HCID 60108777HCID 60108777, compoundYield 108.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
45 °C

Procedure

A solution of 1-(3-benzenesulfonylmethyl-2-nitro-phenyl)-4-methyl-piperazine (25 g) in tetrahydrofuran (500 mL) prepared by heating to 45° C. was added to a pre-hydrogenated suspension of Pearlman's catalyst (20% Pd(OH)2/C; 0.5 g) in tetrahydrofuran (20 mL). Stirring is continued under a hydrogen atmosphere at 45° C. until the reaction is complete (ca. 29 hours). After cooling, the catalyst is filtered off on Solkafloc™ (10 g) and washed with tetrahydrofuran (50 mL). The filtrate is concentrated under vacuum to give 24.9 g of 2-benzenesulfonylmethyl-6-(4-methyl-piperazin-1-yl)-phenylamine as a foam.

Workup

  1. customis continued under a hydrogen atmosphere at 45° C. until the reaction
  2. custom(ca. 29 hours)
  3. temperatureAfter cooling
  4. filtrationthe catalyst is filtered off on Solkafloc™ (10 g)
  5. washwashed with tetrahydrofuran (50 mL)
  6. concentrationThe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-42cab79e162f456992b778abb80545de
Source dataset
uspto-grants-2004_09
Patent number
US06787535B2

Reaction notes

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