sym-Diethylurea → HCID 68828546, compound

HRID 2099348Notes

Reaction equation

HRID 2099348 reaction equation
[CH:1]1([N:7]([C:23]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[O:24])[CH:8]2[CH2:14][CH:13]3[N:15](C(OC(C)(C)C)=O)[CH:10]([CH2:11][CH2:12]3)[CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(NC(NCC)=O)C>Cl.C(OCC)C>[CH:10]12[NH:15][CH:13]([CH2:12][CH2:11]1)[CH2:14][CH:8]([N:7]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[C:23]([N:25]([CH2:26][CH3:27])[CH2:28][CH3:29])=[O:24])[CH2:9]2

Participants

5

Reactant 2

HCID 12194sym-DiethylureaHCID 68828193HCID 68828193, compound

Product 1

HCID 68828546HCID 68828546, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

3.0 g of tert-butyl 3-{cyclohexyl[(diethyl-amino)carbonyl]amino}-8-azabicyclo[3.2.1]octane-8-carboxylate mixed with diethylurea are placed in 37 ml of 2N hydrochloric acid in diethyl ether. The reaction medium is stirred at ambient temperature for 16 h. After evaporation to dryness, the residue is taken up with a 1N aqueous hydrochloric acid solution. Extraction is carried out with ethyl acetate and a 1N aqueous sodium hydroxide solution is then added up to a pH of 10. Extraction is carried out with ethyl acetate until the aqueous phase is completely depleted. The organic phase is washed with H2O and then with a saturated aqueous sodium chloride solution. After drying over MgSO4 and concentration to dryness, 1.8 g of N-8-azabicyclo[3.2.1]oct-3-yl-N-cyclohexyl-N′,N′-diethylurea are obtained.

Workup

  1. customAfter evaporation to dryness
  2. extractionExtraction
  3. additiona 1N aqueous sodium hydroxide solution is then added up to a pH of 10
  4. extractionExtraction
  5. washThe organic phase is washed with H2O
  6. dry with materialAfter drying over MgSO4 and concentration to dryness, 1.8 g of N-8-azabicyclo[3.2.1]oct-3-yl-N-cyclohexyl-N′,N′-diethylurea
  7. customare obtained

Sources & evidence

ORD record
ord-1a3f9abd8d394d0f84b4bd65bc3cdd3b
Source dataset
uspto-grants-2009_08
Patent number
US07569582B2

Reaction notes

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