1-Hydroxybenzotriazole → 4-[4-[4-(cis-2,6-Dimethylmorpholin-4-yl)phenyl]piperazin-1-yl]benzoic acid benzotriazol-1-yl ester

HRID 1816754Notes

Reaction equation

HRID 1816754 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21]4[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=4)[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH2:3]1.O[N:31]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[N:33]=[N:32]1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[N:31]1([O:26][C:25](=[O:27])[C:24]2[CH:28]=[CH:29][C:21]([N:18]3[CH2:17][CH2:16][N:15]([C:12]4[CH:11]=[CH:10][C:9]([N:4]5[CH2:5][C@H:6]([CH3:8])[O:7][C@H:2]([CH3:1])[CH2:3]5)=[CH:14][CH:13]=4)[CH2:20][CH2:19]3)=[CH:22][CH:23]=2)[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[N:33]=[N:32]1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 543123714-[4-[4-(cis-2,6-Dimethylmorpholin-4-yl)phenyl]piperazin-1-yl]benzoic acid

Product 1

HCID 540341114-[4-[4-(cis-2,6-Dimethylmorpholin-4-yl)phenyl]piperazin-1-yl]benzoic acid benzotriazol-1-yl esterYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[4-[4-(cis-2,6-dimethylmorpholin-4-yl)phenyl]piperazin-1-yl]benzoic acid (1.01 g), 1-hydroxybenzotriazole (370 mg) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (986 mg) in methylene chloride (100 ml) was stirred for 4 hours at room temperature then evaporated under reduced pressure. Water was added to the residue and the resulting precipitate collected by filtration, washed with water, then dried under hi-vacuum to give 4-[4-[4-(cis-2,6-dimethylmorpholin-4-yl)phenyl]piperazin-1-yl]benzoic acid benzotriazol-1-yl ester (1.197 g).

Workup

  1. customthen evaporated under reduced pressure
  2. additionWater was added to the residue
  3. filtrationthe resulting precipitate collected by filtration
  4. washwashed with water
  5. customdried under hi-vacuum

Sources & evidence

ORD record
ord-b8c42fa33ebf4e488bd92073a15556a7
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

Loading…