HCID 67255038, compound → HCID 22046321, compound

HRID 1830746Notes

Reaction equation

HRID 1830746 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=1[O:15][CH2:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])(C)(C)C>O1CCOCC1.Cl>[CH3:21][N:19]([CH3:20])[CH2:18][CH2:17][CH2:16][O:15][C:9]1[CH:10]=[CH:11][C:12]([CH3:14])=[CH:13][C:8]=1[NH2:7]

Participants

4

Reactant 1

HCID 67255038HCID 67255038, compound

Product 1

HCID 22046321HCID 22046321, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of [2-(3-dimethylamino-propoxy)-5-methyl-phenyl]-carbamic acid tert-butyl ester (617 mg, 2.0 mmol) in 5 mL of dioxane was added hydrochloric acid (2 mL; 4N in dioxane). After stirring for 12 hours, the reaction was diluted with 20 ml of 1N hydrochloric acid and washed with ethyl acetate (2×30 mL). The aqueous layer was basified with 10% aqueous sodium carbonate (50 mL) and extracted with ethyl acetate (3×50 mL). The ethyl acetate was washed with brine (1×30 mL), then dried (MgSO4), and filtered. The filtered solution was concentrated under reduced to yield the corresponding aniline.

Workup

  1. washwashed with ethyl acetate (2×30 mL)
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe ethyl acetate was washed with brine (1×30 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtered solution was concentrated

Sources & evidence

ORD record
ord-ee79531c619c43e6aacc744fa4e30e6a
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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