Methanol → HCID 19791270, compound

HRID 1655196Notes

Reaction equation

HRID 1655196 reaction equation
Cl.Cl.[C:3]([N:6]1[CH2:11][CH2:10][N:9]([NH2:12])[CH2:8][CH2:7]1)(=[O:5])[CH3:4].C(N(CC)CC)C.[F:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1.CO>ClCCl>[C:3]([N:6]1[CH2:11][CH2:10][N:9]([NH:12][C:28]([NH:27][C:24]2[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=2)=[O:29])[CH2:8][CH2:7]1)(=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 709554-Fluorophenyl isocyanateHCID 21701657HCID 21701657, compound

Product 1

HCID 19791270HCID 19791270, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 1-acetyl-4-aminopiperazine dihydrochloride (540 mg) in dichloromethane (5 ml) was added dropwise triethylamine (0.8 ml) followed by addition a solution of 4-fluorophenylisocyanate (377 mg) in dichloromethane (2.5 ml) with stirring in an ice bath. After stirring for 100 minutes at the same temperature, a mixture of dichloromethane (15 ml) and methanol (3 ml) was added to the reaction mixture. The mixture was washed with brine, dried, and concentrated in vacuo. The residue was crystallized from ethanol to yield N-(4-acetyl-1-piperazinyl)-N'-(4-fluoroph-enyl)urea (500 mg).

Workup

  1. stirringAfter stirring for 100 minutes at the same temperature
  2. additionwas added to the reaction mixture
  3. washThe mixture was washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-a8ec0385cd77455a8699198d80df9991
Source dataset
uspto-grants-1993_10
Patent number
US05250528

Reaction notes

Loading…