Dicyclohexylcarbodiimide → HCID 19880191, compound

HRID 1885264Notes

Reaction equation

HRID 1885264 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[C:9]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:8]([Cl:31])=[CH:7][C:3]=1[C:4](O)=[O:5].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:57][N:58]1[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]1>O1CCCC1>[Cl:1][C:2]1[C:10]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=[C:9]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[C:8]([Cl:31])=[CH:7][C:3]=1[C:4]([N:61]1[CH2:62][CH2:63][N:58]([CH3:57])[CH2:59][CH2:60]1)=[O:5]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 19880184HCID 19880184, compound

Product 1

HCID 19880191HCID 19880191, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,5-dichloro-3,4-bis(p-methoxybenzyloxy)benzoic acid (2.02 g: 4.36 mMol.) and 1-hydroxybenzotriazole (648 mg: 1.1 Eq.) in tetrahydrofuran (40 ml) is added dicyclohexylcarbodiimide (990 mg: 1.1 Eq.), and the mixture is stirred at room temperature for 90 minutes. This solution is mixed with N-methylpiperazine (0.66 g: 1.5 Eq.) and stirred at room temperature for 1 hour. The reaction mixture is filtered to remove solid and concentrated under reduced pressure. The residue is purified by silica gel chromatography to give 1-(2,5-dichloro-3,4-bis(p-methoxybenzyloxy)benzoyl)-4-methylpiperazine (1.7 g) from the fraction eluting with 5% methanol-chloroform. Yield: 71%.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. filtrationThe reaction mixture is filtered
  3. customto remove solid
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-7efd69176b7c4e5d920a2052ce44fd81
Source dataset
uspto-grants-1992_09
Patent number
US05143910

Reaction notes

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