4-Dimethylamino-4-phenyl-cyclohexylamine → 1-(4-dimethylamino-4-phenylcyclohexyl)-3-[2-(1H-indol-3-yl)-1-methylethyl]urea

HRID 1394253Notes

Reaction equation

HRID 1394253 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][CH:26]([CH3:37])[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][CH:26]([CH3:37])[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 69217046[2-(1H-Indol-3-yl)-1-methylethyl]carbamic acid phenyl ester

Product 1

HCID 692169201-(4-dimethylamino-4-phenylcyclohexyl)-3-[2-(1H-indol-3-yl)-1-methylethyl]urea

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The more polar diastereoisomer of N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine (109 mg, 0.5 mmole) was added to a solution of [2-(1H-indol-3-yl)-1-methyl-ethyl]-carbamic acid phenyl ester (147 mg, 0.5 mmole) in dioxane (10 ml). The batch was then refluxed for 6 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-(1H-indol-3-yl)-1-methylethyl]urea was obtained after chromatography on silica gel with methanol as a colorless oil in a yield of 100 mg (48%).

Workup

  1. temperatureThe batch was then refluxed for 6 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-e285a1b29af645e2a2900634fbb65a1a
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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