Ethanol → HCID 20041027, compound

HRID 1762446Notes

Reaction equation

HRID 1762446 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[C:18]=3[NH2:24])[CH2:13][CH2:12]2)=[O:7])=[CH:4][CH:3]=1.[C:27](N1C=CN=C1)(N1C=CN=C1)=[O:28].C(O)C>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]3[C:18]4[NH:24][C:27](=[O:28])[NH:23][C:19]=4[CH:20]=[CH:21][CH:22]=3)[CH2:13][CH2:12]2)=[O:7])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 682631,1'-CarbonyldiimidazoleHCID 20041024HCID 20041024, compound

Product 1

HCID 20041027HCID 20041027, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

10 Mmol (3.57 g) of 4-fluoro-N-[2-{4-(2,3-diaminophenyl)-1-piperazinyl}ethyl]benzamide were dissolved in 35 ml of tetrahydrofuran (which had been distilled over LiAlH4), and the solution was cooled in an ice-bath to 0° C. under an atmosphere of nitrogen. 21 Mmol (3.4 g) of 1,1'-carbonyldiimidazole in 20 ml of tetrahydrofuran was added in one portion to this solution while vigorously stirring. The temperature raised to 10° C. Thereafter the mixture was stirred for 3 hours at room temperature. The reaction mixture was evaporated to dryness under reduced pressure, the residue was taken up into chloroform, and the solution was washed with water. The organic layer was evaporated to dryness, and the residue was chromatographed over silicagel with a mixture of methylene chloride, methanol and 25% of ammonia (92:7.5:0.5) as the eluent. The so obtained base was cyrstallized from ethanol, and the title compound was obtained having a melting-point of 240°-243.5° C.

Workup

  1. temperatureThe temperature raised to 10° C
  2. stirringThereafter the mixture was stirred for 3 hours at room temperature
  3. customThe reaction mixture was evaporated to dryness under reduced pressure
  4. washthe solution was washed with water
  5. customThe organic layer was evaporated to dryness
  6. customthe residue was chromatographed over silicagel with a mixture of methylene chloride, methanol and 25% of ammonia (92:7.5:0.5) as the eluent
  7. customThe so obtained base

Sources & evidence

ORD record
ord-b8e44844a9b04b1bb06af1fadff41849
Source dataset
uspto-grants-1989_05
Patent number
US04833142

Reaction notes

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