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Water → 5-amino-2,4-dimethyl-N-(pyridin-3-ylmethyl)benzenesulfonamide

HRID 1802463
Notes
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Reaction equation

HRID 1802463 reaction equation
C1C2C(COC(=O)[NH:17][C:18]3[CH:23]=[C:22]([S:24]([NH:27][CH2:28][C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)(=[O:26])=[O:25])[C:21]([CH3:35])=[CH:20][C:19]=3[CH3:36])C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1.O.CCOC(C)=O>CC(N(C)C)=O>[NH2:17][C:18]1[C:19]([CH3:36])=[CH:20][C:21]([CH3:35])=[C:22]([S:24]([NH:27][CH2:28][C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)(=[O:26])=[O:25])[CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 8857Ethyl AcetateHCID 594361089H-fluoren-9-ylmethyl(2,4-dimethyl-5-{[(pyridin-3-ylmethyl)amino]sulfonyl}phenyl)carbamate

Product 1

HCID 594360245-amino-2,4-dimethyl-N-(pyridin-3-ylmethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 31374
Dimethylacetamide
Solvent

Procedure

To a solution of 9H-fluoren-9-ylmethyl(2,4-dimethyl-5-{[(pyridin-3-ylmethyl)amino]sulfonyl}phenyl)carbamate (1.2 g, 2.3 mmol) in DMA (4.5 mL) was added piperidine (0.8 mL, 7.9 mmol). The reaction stirred at room temperature for one hour and was then poured into a separatory funnel containing water and EtOAc. The reaction was extracted with EtOAc and the organic extracts were dried over Na2SO4 and concentrated in vacuo.

Workup

  1. additionwas then poured into a separatory funnel
  2. extractionThe reaction was extracted with EtOAc
  3. dry with materialthe organic extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c5bab947c37948ab97be4a123bffa7da
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08349865B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes