Potassium Hydroxide → HCID 13036368, compound

HRID 128077Notes

Reaction equation

HRID 128077 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:13]=[C:14]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=[C:15]3[N:16]=2)[CH2:8][CH2:7]1)=O)C.[OH-].[K+]>C(O)C.O>[N:9]1([C:12]2[N:16]=[C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[N:13]=2)[CH2:10][CH2:11][NH:6][CH2:7][CH2:8]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 13653113HCID 13653113, compound

Product 1

HCID 13036368HCID 13036368, compoundYield 126.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 4-(2-cycloheptimidazolyl)-piperazine-1-carboxylic acid ethyl ester (2.86 g, described in Example 1) and potassium hydroxide in ethanol (20 ml) and water (1.5 ml) was refluxed for 20 hr. Water was added and the ethanol was evaporated. Additional water was added and the solution was extracted with chloroform. The organic extract was dried and evaporated to give the title compound (2.7 g). To a solution of the title compound in chloroform and diethyl ether, a solution of hydrogen chloride in diethyl ether was added. The precipitate was collected and crystallized from methanol-diethyl ether to obtain the hydrochloride salt of the title compound (2.4 g): mp>280° C.; ir(nujol) 2600, 1630 and 1584 cm-1 ; uv max (MeOH) 285(ε7540), 261(ε26,930) and 236 nm(ε18,310) and nmr(DMSO-d6)δ 3.37(4H,t), 4.3(4H,t), 8.4(5H,m) and 10.0(2H,s).

Workup

  1. temperaturewas refluxed for 20 hr
  2. customthe ethanol was evaporated
  3. additionAdditional water was added
  4. extractionthe solution was extracted with chloroform
  5. extractionThe organic extract
  6. customwas dried
  7. customevaporated

Sources & evidence

ORD record
ord-e0c14630c92d4997a600a6aca555326e
Source dataset
uspto-grants-1981_03
Patent number
US04258188

Reaction notes

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