Dicyclohexylcarbodiimide → HCID 19880152, compound

HRID 1885258Notes

Reaction equation

HRID 1885258 reaction equation
[Cl:1][C:2]1[C:3]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[C:4]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH:5]=[C:6]([CH:10]=1)[C:7](O)=[O:8].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:56][N:57]1[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]1>O1CCCC1>[Cl:1][C:2]1[C:3]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[C:4]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[CH:5]=[C:6]([CH:10]=1)[C:7]([N:60]1[CH2:61][CH2:62][N:57]([CH3:56])[CH2:58][CH2:59]1)=[O:8]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 19880177HCID 19880177, compound

Product 1

HCID 19880152HCID 19880152, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-chloro-3,4-bis(p-methoxybenzyloxy)benzoic acid (0.75 g: 1.75 mMol.) and 1-hydroxybenzotriazole (0.26 g: 1.1 Eq.) in tetrahydrofuran (15 ml) is added dicyclohexylcarbodiimide (0.40 g: 1.1 Eq.). After 1 hour stirring, to the mixture is added N-methylpiperazine (0.44 ml: 2.3 Eq.), and the mixture is stirred for 1 hour. The reaction mixture is filtered to remove solid and concentrated under reduced pressure to give 1-(5-chloro-3,4-bis(p-methoxybenzyloxy)benzoyl)-4-methylpiperazine (0.86 g). Yield: 96%.

Workup

  1. stirringthe mixture is stirred for 1 hour
  2. filtrationThe reaction mixture is filtered
  3. customto remove solid
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-31bb6a21536d43a99f87e820844269a5
Source dataset
uspto-grants-1992_09
Patent number
US05143910

Reaction notes

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