HCID 12986252, compound → HCID 10025689, compound

HRID 1394261Notes

Reaction equation

HRID 1394261 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][CH2:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=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][CH2:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:24])[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 12986252HCID 12986252, compoundHCID 21082146(4-Aminomethyl-1-phenylcyclohexyl)dimethylamine

Product 1

HCID 10025689HCID 10025689, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The diastereoisomer mixture of (4-aminomethyl-1-phenyl-cyclohexyl)-dimethylamine (465.8 mg, 2.0 mmole) was added to a solution of (3-phenylpropyl)carbamic acid phenyl ester (510.6 mg, 2.0 mmole) in dioxane (15 ml). The batch was then refluxed for 12 h. Working up was performed by removing dioxane by distillation in a rotary evaporator and combining the residue with water (10 ml). The batch was adjusted to pH 11 with 5M NaOH and extracted with EE (3×20 ml). The combined EE extracts were washed with 1M NaOH (1×5 ml) and dried with Na2SO4. The solvent was removed by distillation under a vacuum. The residue was the diastereoisomer mixture of 1-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-(3-phenyl-propyl)-urea, which was separated and purified by flash chromatography on silica gel (60 g). Ethanol/EE (1:1, 1100 ml) was used as eluent. The more nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-(3-phenyl-propyl)-urea (310 mg, yellow oil, 39%) and the more polar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-(3-phenyl-propyl)-urea (55 mg, m.p. 159-165° C., 32%) were isolated in this manner.

Workup

  1. temperatureThe batch was then refluxed for 12 h
  2. customby removing dioxane
  3. distillationby distillation
  4. customin a rotary evaporator
  5. extractionextracted with EE (3×20 ml)
  6. washThe combined EE extracts were washed with 1M NaOH (1×5 ml)
  7. dry with materialdried with Na2SO4
  8. customThe solvent was removed by distillation under a vacuum
  9. additionthe diastereoisomer mixture of 1-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-(3-phenyl-propyl)-urea, which
  10. customwas separated
  11. custompurified by flash chromatography on silica gel (60 g)

Sources & evidence

ORD record
ord-0e40ff39b11443e8a086333c93fc1be6
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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