(4-Aminomethyl-1-phenylcyclohexyl)dimethylamine → 1-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-[2-(1H-indol-3-yl)-1-methyl-ethyl]-urea

HRID 1394265Notes

Reaction equation

HRID 1394265 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>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

4

Reactant 2

HCID 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 polar 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. A precipitate formed at RT. The precipitate was filtered out, and washed once with cold dioxane (2 ml) and with diethyl ether (3×3 ml). The more polar 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 140-146° C. in a yield of 231 mg (76%).

Workup

  1. temperatureThe batch was then refluxed for 14 h
  2. customA precipitate formed at RT
  3. filtrationThe precipitate was filtered out
  4. washwashed once with cold dioxane (2 ml) and with diethyl ether (3×3 ml)

Sources & evidence

ORD record
ord-068380ab49b643449a3cab8823e7a969
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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