Hydrochloric Acid → HCID 69671045, compound

HRID 1951481Notes

Reaction equation

HRID 1951481 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N:12]([CH3:26])[CH:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]1.Cl>C(O)(C)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N:12]([CH3:26])[CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67303719HCID 67303719, compound

Product 1

HCID 69671045HCID 69671045, compoundYield 114.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
42.5 °C

Procedure

To a 250 mL three neck round bottom flask, added 2-Methoxy-5-nitro-N-methyl-N-(1-Boc piperidine-4-yl)phenyl amine (3 grams, 8.21 mmol) obtained at step (II), followed by the addition of isopropyl alcohol (20 mL) and allowed to stir for 10 minutes. The reaction mass was heated to 40-45° C. and stirred for 5 minutes to get a clear solution. Isopropanolic hydrogenchloride, (20%) solution (15.99 mL, 65.75 mmol) was added to the above reaction mass, drop-wise over a period of 10 minutes. Further the reaction mass was heated at 60-63° C. for 2 hours. The solids that separated were filtered and taken into water (20 mL), basified with ammonia solution and extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with brine solution (20 mL), dried over sodium sulfate and solvent was removed under reduced pressure to obtain 2.5 grams of the title product.

Workup

  1. customobtained at step (II)
  2. stirringstirred for 5 minutes
  3. customto get a clear solution
  4. temperatureFurther the reaction mass was heated at 60-63° C. for 2 hours
  5. customThe solids that separated
  6. filtrationwere filtered
  7. extractionextracted with ethyl acetate (3×50 mL)
  8. washThe combined organic layer was washed with brine solution (20 mL)
  9. dry with materialdried over sodium sulfate and solvent
  10. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-ed79d52acb444ddba34a70a8eeef8456
Source dataset
uspto-grants-2013_03
Patent number
US08404720B2

Reaction notes

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