Ethanol → HCID 21397158, compound

HRID 1439368Notes

Reaction equation

HRID 1439368 reaction equation
C(O)C.[F:4][C:5]([F:41])([F:40])[C:6]1[CH:39]=[CH:38][C:9]([C:10]([NH:12][C:13]2[N:17]([CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][N:24](CC4C=CC=CC=4)[CH2:23][CH2:22]3)[C:16]3[CH:34]=[CH:35][CH:36]=[CH:37][C:15]=3[N:14]=2)=[O:11])=[CH:8][CH:7]=1.[H][H]>[Pd].C(O)(=O)C>[F:40][C:5]([F:4])([F:41])[C:6]1[CH:39]=[CH:38][C:9]([C:10]([NH:12][C:13]2[N:17]([CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[C:16]3[CH:34]=[CH:35][CH:36]=[CH:37][C:15]=3[N:14]=2)=[O:11])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 21397144HCID 21397144, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21397158HCID 21397158, compoundYield 63.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution composed of 75 ml. ethanol and 1 ml. glacial acetic acid was added 2-(4-trifluoromethylbenzamido)-1-[3-(4-benzyl-1-piperazinyl)propyl]benzimidazole (500 mg., 0.96 millimole) and 100 mg. of 10% Pd/C catalyst. The mixture was shaken on a Paar apparatus at about 2 atm. pressure of hydrogen and 40° C. for 2.5 hrs. at which time the reaction was complete. The catalyst was removed by filtration and the filtrate was evaporated in vacuo to yield a white solid, which on trituration under acetone yielded 300 mg. (63.9% yield) of 2-(4-trifluoromethylbenzamido)-1-[3-(1-piperazinyl)propyl]benzimidazole, as a white crystalline solid, m.p. 184°-185° C.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated in vacuo
  3. customto yield a white solid, which on trituration under acetone
  4. customyielded 300 mg

Sources & evidence

ORD record
ord-a434c885a8684ef48165901c6dce3964
Source dataset
uspto-grants-1977_11
Patent number
US04059584

Reaction notes

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