4-Dimethylamino-4-phenyl-cyclohexylamine → HCID 69217077, compound

HRID 1394258Notes

Reaction equation

HRID 1394258 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]=[C:34]([F:37])[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]=[C:34]([F:37])[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 69217510HCID 69217510, compound

Product 1

HCID 69217077HCID 69217077, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The more polar diastereoisomer of 4-dimethylamino-4-phenyl-cyclohexylamine (271 mg, 1.24 mmole) was added to a solution of [2-(5-fluoro-1H-indol-3-yl)-ethyl]-carbamic acid phenyl ester (370 mg, 1.24 mmole) in dioxane (20 ml). The batch was then refluxed for 8 h. Working up was performed by removing dioxane by distillation and diluting the batch with water (10 ml). The batch was adjusted to pH 11 with 5M NaOH and extracted with EE (3×20 ml). The organic phase was dried with Na2SO4 and evaporated. The more polar diastereoisomer of 1-(4-dimethylamino-4-phenylcyclohexyl)-3-[2-(5-fluoro-1H-indol-3-yl)ethyl]urea was obtained after chromatography on silica gel with methanol as a colorless oil in a yield of 267 mg (51%).

Workup

  1. temperatureThe batch was then refluxed for 8 h
  2. customby removing dioxane
  3. distillationby distillation
  4. additiondiluting the batch with water (10 ml)
  5. extractionextracted with EE (3×20 ml)
  6. dry with materialThe organic phase was dried with Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-be81b1c2df4941bba5324975858f3a5d
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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