Hydrochloric Acid → HCID 22254652, compound

HRID 1611656Notes

Reaction equation

HRID 1611656 reaction equation
[CH3:1][S:2]([C:5]1[CH:32]=[CH:31][C:8]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:12][CH2:11]2)=[C:7]([N+:33]([O-])=O)[CH:6]=1)(=[O:4])=[O:3].Cl>CO>[NH2:33][C:7]1[CH:6]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:32]=[CH:31][C:8]=1[NH:9][CH:10]1[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22254649HCID 22254649, compound

Product 1

HCID 22254652HCID 22254652, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
95 °C

Procedure

To a stirred solution of 4-methanesulphonyl-2-nitro-1-N-[1-(3,3-diphenylpropyl)-piperidin-4-yl]aniline (200 mg, 0.4 mmol) in methanol (4 ml) was added concentrated HCl (1 ml) followed by stannous chloride dihydrate (620 mg) and the mixture was heated to 95° C. After 3 h the reaction mixture was concentrated and suspended in water (100 ml) and potassium carbonate was added to basify the solution. The solution was extracted with EtOAc (150 ml) and the emulsion left to separate. The mixture was then filtered through Celite™, separated, dried (MgSO4), concentrated and purified by Bond Elut™ chromatography (using 1% to 7.5% EtOH in DCM) to give the title compound as an oil (50 mg, 0.11 mmol); MS: 464.

Workup

  1. concentrationAfter 3 h the reaction mixture was concentrated
  2. additionpotassium carbonate was added
  3. extractionThe solution was extracted with EtOAc (150 ml)
  4. waitthe emulsion left
  5. customto separate
  6. filtrationThe mixture was then filtered through Celite™
  7. customseparated
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. custompurified by Bond Elut™ chromatography (using 1% to 7.5% EtOH in DCM)

Sources & evidence

ORD record
ord-7571fbb4440e4a74b3b28bc4c5a12256
Source dataset
uspto-grants-2006_01
Patent number
US06989393B2

Reaction notes

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