Hydrochloric Acid → HCID 23000985, compound

HRID 397742Notes

Reaction equation

HRID 397742 reaction equation
[CH2:1]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH:19]C(=O)C(O)(C)C)[CH:14]=2)[CH2:9][CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Cl>O1CCOCC1.O>[NH2:19][C:15]1[CH:14]=[C:13]([CH:10]2[CH2:11][CH2:12][N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:8][CH2:9]2)[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 23001068HCID 23001068, compound

Product 1

HCID 23000985HCID 23000985, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of N-hexyl-4-(3-(2-hydroxy-2-methylpropanoylamino)phenyl)piperidine (Example 158) in 1,4-dioxan:5N aqueous hydrochloric acid solution (1:1, 10 ml) was heated under reflux overnight. The reaction mixture was cooled, diluted with water (10 ml) and extracted with diethyl ether (3×10 ml). The pH of the aqueous layer was adjusted to 8-9 using 5N aqueous sodium hydroxide, and extracted with dichloromethane (5×10 ml). The combined extracts were washed with brine (10 ml), dried (Na2SO4) and concentrated in vacuo to give the title compound as an oil which was not purified further (178 mg, 61% over two steps).

Workup

  1. temperatureunder reflux overnight
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with diethyl ether (3×10 ml)
  4. extractionextracted with dichloromethane (5×10 ml)
  5. washThe combined extracts were washed with brine (10 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5cba0c1961d44f6790a509783b3bd4b5
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

Loading…