Dicyclohexylcarbodiimide → HCID 86746099, compound

HRID 1885262Notes

Reaction equation

HRID 1885262 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[C:4]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.[CH3:56][N:57]1[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]1>O1CCCC1>[Cl:1][C:2]1[C:7]([C:8]([N:60]2[CH2:61][CH2:62][N:57]([CH3:56])[CH2:58][CH2:59]2)=[O:10])=[CH:6][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[C:4]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 19880183HCID 19880183, compound

Product 1

HCID 86746099HCID 86746099, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-chloro-3,4-bis(p-methoxybenzyloxy)benzoic acid (94 g: 218 mMol.) in tetrahydrofuran (1 liter) are added dicyclohexylcarbodiimide (50 g: 1.1 Eq.) and N-hydroxybenzotriazole (33 g: 1.1 Eq.), and the mixture is stirred at room temperature for 90 minutes. To the reaction mixture is added N-methylpiperazine (48 ml: 2 Eq.) and the resulting precipitate is filtered off. The filtrate is concentrated under reduced pressure, diluted with ethyl acetate, washed with aqueous sodium hydroxide and water, dried and concentrated in vacuum. The residue is treated in dichloromethane and ether to remove a small amount of insoluble material and concentrated under reduced pressure to give 1-(6-chloro-3,4-bis(p-methoxybenzyloxy)benzoyl-4-methylpiperazine (108 g). Yield: 97%.

Workup

  1. filtrationthe resulting precipitate is filtered off
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. additiondiluted with ethyl acetate
  4. washwashed with aqueous sodium hydroxide and water
  5. customdried
  6. concentrationconcentrated in vacuum
  7. additionThe residue is treated in dichloromethane
  8. customether to remove a small amount of insoluble material
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d11d5cc3531447fba5490db16f172e81
Source dataset
uspto-grants-1992_09
Patent number
US05143910

Reaction notes

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