Norchlorcyclizine → Cetirizine ethyl ester

HRID 1871007

반응식

HRID 1871007 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.Cl[CH2:22][CH2:23][O:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:9]2[CH2:10][CH2:11][N:12]([CH2:22][CH2:23][O:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:13][CH2:14]2)=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 9340NorchlorcyclizineHCID 10964894Ethyl 2-(2-chloroethoxy)acetate

생성물 1

HCID 9844843Cetirizine ethyl ester수율 89%

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

The present inventors have found that when the reaction is performed in a tertiary amine as both solvent and acid scavenger at elevated temperature, significantly higher yield is obtained. Namely, when 1-[(4-chlorophenyl)phenylmethyl]piperazine is reacted in a pressure vessel with ethyl 2-chloroethoxyacetate in triethylamine at 135° C. for 10 hours, ethyl [2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetate is obtained in 89% yield. When catalytic amounts of potassium iodide or tetrabutylammonium iodide are present in the reaction, slightly higher yield is obtained. If triisopropylamine or pyridine are used instead of triethylamine and the reaction is carried out at the same temperature at atmospheric pressure, a drop of 30-40% in the reaction yield is observed.

후처리

  1. customacid scavenger at elevated temperature, significantly higher yield
  2. customis obtained

출처 및 근거

ORD 기록
ord-edd692d347b74356a96619ef7662d27f
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06100400

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