Sodium Hydroxide → 1-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-[2-(1H-indol-3-yl)-1-methyl-ethyl]-urea

HRID 1394264Notes

Reaction equation

HRID 1394264 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][C:6]([N:15]([CH3:17])[CH3:16])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.C1([O:24][C:25](=O)[NH:26][CH:27]([CH3:38])[CH2:28][C:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[NH:31][CH:30]=2)C=CC=CC=1.[OH-].[Na+]>O1CCOCC1>[CH3:16][N:15]([CH3:17])[C:6]1([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:5][CH2:4][CH:3]([CH2:2][NH:1][C:25]([NH:26][CH:27]([CH3:38])[CH2:28][C:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[NH:31][CH:30]=2)=[O:24])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21082146(4-Aminomethyl-1-phenylcyclohexyl)dimethylamineHCID 69217046[2-(1H-Indol-3-yl)-1-methylethyl]carbamic acid phenyl ester

Product 1

HCID 117544171-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-[2-(1H-indol-3-yl)-1-methyl-ethyl]-urea

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The more nonpolar diastereoisomer of (4-aminomethyl-1-phenyl-cyclohexyl)-dimethylamine (162.7 mg, 0.7 mmole) was added to a solution of [2-(1H-indol-3-yl)-1-methyl-ethyl]-carbamic acid phenyl ester (206 mg, 0.7 mmole) in dioxane (7 ml). The batch was then refluxed for 14 h. Working up was performed by pouring the reaction mixture into ice water (15 ml), adjusting the pH to 11 with 5M NaOH and extracting with ether (3×20 ml). The organic phase was dried with Na2SO4 and then evaporated. The residue was purified by flash chromatography on silica gel (30 g). Ethanol/EE (1:2, 400 ml) was used as eluent. The more nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-[2-(1H-indol-3-yl)-1-methyl-ethyl]-urea was obtained in this manner as a colorless solid with a melting point of 89-92° C. in a yield of 185 mg (61%).

Workup

  1. temperatureThe batch was then refluxed for 14 h
  2. extractionextracting with ether (3×20 ml)
  3. dry with materialThe organic phase was dried with Na2SO4
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel (30 g)

Sources & evidence

ORD record
ord-a05ef9a240b242ec80b5d42854d6eb7f
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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