4-Dimethylamino-4-phenyl-cyclohexylamine → HCID 12986254, compound

HRID 1394237Notes

Reaction equation

HRID 1394237 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][C:28]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[NH:30][CH:29]=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][C:28]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[NH:30][CH:29]=2)=[O:23])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 129862564-Dimethylamino-4-phenyl-cyclohexylamineHCID 60628064HCID 60628064, compound

Product 1

HCID 12986254HCID 12986254, 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 [2-(1H-indol-3-yl)ethyl]carbamic acid phenyl ester (280 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 product was obtained as a colorless oil in a yield of 404 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 product was obtained as a colorless oil in a yield of 404 mg (100%)

Sources & evidence

ORD record
ord-c6ea66ab03784072b873b60b768eb4a4
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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