Diethylamine → 1,3-dihydro-4-(3-methoxyphenyl)-1-(4-piperidinyl)-2H-imidazol-2-one

HRID 1782687Notes

Reaction equation

HRID 1782687 reaction equation
[C:1]1([C:7]2[NH:8][C:9](=[O:35])[N:10]([CH:12]3[CH2:17][CH2:16][N:15](C(OCC4C5C=CC=CC=5C5C4=CC=CC=5)=O)[CH2:14][CH2:13]3)N=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:36]1CCC[CH2:37]1.[CH2:41](NCC)C>CO>[CH3:37][O:36][C:5]1[CH:6]=[C:1]([C:7]2[NH:8][C:9](=[O:35])[N:10]([CH:12]3[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]3)[CH:41]=2)[CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 8028TetrahydrofuranHCID 1356275992,4-dihydro-5-phenyl-2-[1-(9H-fluoren-9-ylmethoxycarbonyl)-4-piperidinyl]-3H-1,2,4-triazol-3-one

Product 1

HCID 183215721,3-dihydro-4-(3-methoxyphenyl)-1-(4-piperidinyl)-2H-imidazol-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 9.0 g (0.0193 mol) of 2,4-dihydro-5-phenyl-2-[1-(9H-fluoren-9-ylmethoxycarbonyl)-4-piperidinyl]-3H-1,2,4-triazol-3-one, 50 ml of tetrahydrofuran and 70 ml of diethylamine was stirred at room temperature until the end of the reaction monitored by thin layer chromatography. The solvent was removed in vacuo, the residue remaining was mixed with 300 ml of water and subjected to ultrasound treatment for 30 minutes. The insoluble matter was separated off by suction filtering and the aqueous filtrate was evaporated down in vacuo. The residue thus obtained was boiled with a little methanol and after cooling it was suction filtered. After drying 0.58 g (12.3% of theory) of colourless crystals of melting point 294° C. (D) and Rf=0.1 (eluant 1) were obtained.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue remaining was mixed with 300 ml of water
  3. customThe insoluble matter was separated off by suction
  4. filtrationfiltering
  5. customthe aqueous filtrate was evaporated down in vacuo
  6. customThe residue thus obtained
  7. temperatureafter cooling it
  8. filtrationfiltered
  9. dry with materialAfter drying 0.58 g (12.3% of theory) of colourless crystals of melting point 294° C. (D)

Sources & evidence

ORD record
ord-9ead69204b774477a7b81d6b89c7fb2e
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

Loading…