Hydrochloric Acid → HCID 22254647, compound

HRID 1611658Notes

Reaction equation

HRID 1611658 reaction equation
[C:1]([C:3]1[CH:30]=[CH:29][C:6]([NH:7][CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:10][CH2:9]2)=[C:5]([N+:31]([O-])=O)[CH:4]=1)#[N:2].Cl>CO>[NH2:31][C:5]1[CH:4]=[C:3]([C:1]#[N:2])[CH:30]=[CH:29][C:6]=1[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22254642HCID 22254642, compound

Product 1

HCID 22254647HCID 22254647, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
95 °C

Procedure

To a stirred solution of 4-cyano-2-nitro-1-N-[1-(3,3-diphenylpropyl)-piperidin-4-yl]aniline (300 mg, 0.68 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 (60 mg, 0.15 mmol); MS: 411.

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-b11268c2dc704b428a8c5a26e86e509b
Source dataset
uspto-grants-2006_01
Patent number
US06989393B2

Reaction notes

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