HCID 12986252, compound → HCID 12986253, compound

HRID 1394235Notes

Reaction equation

HRID 1394235 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][CH:6]([NH2:9])[CH2:5][CH2:4]1.C1([O:23][C:24](=O)[NH:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)C=CC=CC=1>O1CCOCC1>[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][CH:6]([NH:9][C:24]([NH:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:23])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 12986252HCID 12986252, compoundHCID 129862564-Dimethylamino-4-phenyl-cyclohexylamine

Product 1

HCID 12986253HCID 12986253, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-Dimethylamino-4-phenyl-cyclohexylamine (more polar diastereomer) (218 mg, 1.0 mmole) was added to a solution of (3-phenylpropyl)carbamic acid phenyl ester (255 mg, 1.0 mmole) in dioxane and refluxed for 12 h. Working up was performed by removing the dioxane by distillation and combining the residue with water. The batch was adjusted to pH 11 with 5M NaOH and extracted with ethyl acetate. The organic phase was dried with Na2SO4 and evaporated. The more polar product was obtained as a colorless oil in a yield of 379 mg (100%).

Workup

  1. temperaturerefluxed for 12 h
  2. customby removing the dioxane
  3. distillationby distillation
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried with Na2SO4
  6. customevaporated
  7. customThe more polar product was obtained as a colorless oil in a yield of 379 mg (100%)

Sources & evidence

ORD record
ord-5a105e49f4b74e09a2b42dd5f7df8310
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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