4-Hydroxybenzoic Acid → HCID 68561454, compound

HRID 1642099Notes

Reaction equation

HRID 1642099 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[OH:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=1.[Cl:23][C:24]1[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=1[N:31]1[CH2:36][CH2:35][N:34]([CH2:37][CH:38]=[CH:39][CH2:40][NH2:41])[CH2:33][CH2:32]1.C(Cl)(Cl)Cl>N1C=CC=CC=1.CC=C(C)C>[Cl:23][C:24]1[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=1[N:31]1[CH2:32][CH2:33][N:34]([CH2:37][CH:38]=[CH:39][CH2:40][NH:41][C:18](=[O:20])[C:17]2[CH:16]=[CH:15][C:14]([OH:13])=[CH:22][CH:21]=2)[CH2:35][CH2:36]1

Participants

7

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 6212ChloroformHCID 682631,1'-CarbonyldiimidazoleHCID 66756046HCID 66756046, compound

Product 1

HCID 68561454HCID 68561454, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 105532-Methyl-2-buteneSolvent

Procedure

1,1′-carbonyldiimidazole (0.18 g, 1.1 mmol) was added to a solution of the 4-hydroxy benzoic acid (0.15 g, 1.1 mmol) in absolute pyridine and the mixture was stirred at room temperature under Argon for 1 h. After that time a solution of 4-[4-(2,3-Dichloro-phenyl)-piperazin-1-yl]-but-2-enylamine (0.33 g, 1.1 mmol) in 3 ml amylene-stabilized chloroform was added and the mixture was stirred overnight. All volatiles were removed in vacuo and the residue was purified by chromatography to give 0.23 g (51%) of the title compound.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred overnight
  3. customAll volatiles were removed in vacuo
  4. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-3bce029d04b349f6970c9e74a0315110
Source dataset
uspto-grants-2012_02
Patent number
US08119642B2

Reaction notes

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