Hydrochloric Acid → HCID 67303272, compound

HRID 1951483Notes

Reaction equation

HRID 1951483 reaction equation
O.Cl.CO[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[N:14]([CH3:22])[CH:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1.[OH-].[Na+].[CH2:25]([OH:27])C>[Fe]>[CH3:25][O:27][C:9]1[CH:10]=[CH:5][C:6]([N:14]([CH3:22])[CH:15]2[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]2)=[CH:7][C:8]=1[NH2:11]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 962Water2×HCID 14798Sodium HydroxideHCID 67309659HCID 67309659, compound

Product 1

HCID 67303272HCID 67303272, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Conditions

Temperature
50 °C

Procedure

To a 250 mL three necked round bottomed flask, added iron powder (1.99 grams, 6.81 mmol) and 10 mL of demineralized water. Stirred the mass for 5 minutes and added concentrated hydrochloric acid (12 mL) drop-wise. The reaction was exothermic. Further, heated the reaction mass to 50° C. and added a solution of 2-methoxy-5-nitro-N-methyl-N-(1-methyl piperidin-4-yl)phenylamine (1.9 grams, 6.81 mmol) obtained at step (IV) was dissolved in ethanol (20 mL), drop-wise through addition funnel. The reaction mass was heated at 78-80° C. for 4 hours. After completion of reaction (thin layer chromatography), ethanol was distilled off completely under reduced pressure to obtain oily mass. Added water (50 mL) and basified to pH: 9 using 50% aqueous sodium hydroxide solution. Filtered the inorganic and washed the cake with ethyl acetate (2×50 mL). The organic layer was separated and dried over anhydrous sodium sulfate and concentrated to obtain 2.31 grams of oily product.

Workup

  1. customobtained at step (IV)
  2. additiondrop-wise through addition funnel
  3. temperatureThe reaction mass was heated at 78-80° C. for 4 hours
  4. distillationwas distilled off completely under reduced pressure
  5. customto obtain oily mass
  6. filtrationFiltered the inorganic
  7. washwashed the cake with ethyl acetate (2×50 mL)
  8. customThe organic layer was separated
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-9d1f31d215104870a26ad66f736a12e8
Source dataset
uspto-grants-2013_03
Patent number
US08404720B2

Reaction notes

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