1-Phenylpiperazine → HCID 86742246, compound

HRID 580516Notes

Reaction equation

HRID 580516 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]([CH2:16][C:17]1[CH:18]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])[C:19]([C:25]([OH:27])=O)=[C:20]([CH3:24])[NH:21][C:22]=1[CH3:23])([OH:15])=[O:14].[CH:35]1[CH:36]=[CH:37][C:38]([N:41]2[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)=[CH:39][CH:40]=1>O1CCCC1>[C:38]1([N:41]2[CH2:46][CH2:45][N:44]([C:25]([C:19]3[CH:18]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[Cl:34])[C:17]([CH2:16][C:13]([OH:15])=[O:14])=[C:22]([CH3:23])[NH:21][C:20]=3[CH3:24])=[O:27])[CH2:43][CH2:42]2)[CH:39]=[CH:40][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 682631,1'-CarbonyldiimidazoleHCID 20133937HCID 20133937, compound

Product 1

HCID 86742246HCID 86742246, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.1 g (6.5 mmol) of carbonyldiimidazole are added to 1.60 g (5 mmol) of 5-carboxymethyl-4-(2-chlorophenyl)-1,4-dihydro-2,6-dimethyl-pyridine-3-carboxylic acid suspended in 20 ml of absolute tetrahydrofuran. The mixture is stirred at room temperature for 30 minutes and at a reflux temperature for 30 minutes. 1.62 g (10 mmol) of phenylpiperazine in 5 ml of absolute tetrahydrofuran are added to the resulting solution. This mixture is heated to reflux for 3.5 hours and then evaporated, the residue is taken up in methylene chloride, and the solution is washed successively with 1N hydrochloric acid, 1N sodium hydroxide solution and water, dried with magnesium sulphate and again evaporated. The residue crystallizes from isopropanol.

Workup

  1. temperatureThis mixture is heated
  2. temperatureto reflux for 3.5 hours
  3. customevaporated
  4. washthe solution is washed successively with 1N hydrochloric acid, 1N sodium hydroxide solution and water
  5. dry with materialdried with magnesium sulphate
  6. customagain evaporated
  7. customThe residue crystallizes from isopropanol

Sources & evidence

ORD record
ord-054d7b9dd230437b8bd443a4da3528fc
Source dataset
uspto-grants-1988_06
Patent number
US04753936

Reaction notes

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