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Potassium Carbonate → 1-(4-Hydroxyphenyl)-4-(benzoxazol-2-ylmethyl)piperazine

HRID 620043
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HRID 620043 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[CH2:15][C:16]1[O:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:15][C:16]3[O:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1
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참가 물질

5

반응물 3

HCID 11430Potassium Carbonate2회HCID 92467p-(1-Piperazinyl)phenolHCID 20619892-(Chloromethyl)-1,3-benzoxazole

생성물 1

HCID 48066221-(4-Hydroxyphenyl)-4-(benzoxazol-2-ylmethyl)piperazine수율 71.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

A mixture of 6.06 g (34 mmol) of 1-(4-hydroxyphenyl)piperazine and 5.36 g (32 mmol) of 2-chloromethylbenzoxazole in 100 ml of absolute DMF was warmed to 80° C., and 737 mg of powdered K2CO3 were added with stirring (under a nitrogen atmosphere) in each case after 10 minutes, after a further 25 minutes and after a further 60 minutes (total addition of 2.21 g (16 mmol) of K2CO3). The mixture was stirred for a further 3 hours at 80° C., the DMF was substantially removed by distillation in vacuo, and the residue was taken up in 200 ml of ether and 100 ml of water. After separating the phases, the aqueous phase was extracted a further twice with ether. The combined ether extracts were dried, filtered and evaporated in vacuo. The residue was taken up in diisopropyl ether, whereafter crystallization occurred. The crystalline substance was filtered off under suction. 7.10 g (71.7% of theory) of 1-(4-hydroxyphenyl)-4-(benzoxazol-2-ylmethyl)piperazine, melting point 155°-56° C., were obtained,

후처리

  1. waitafter a further 25 minutes
  2. stirringThe mixture was stirred for a further 3 hours at 80° C.
  3. customthe DMF was substantially removed by distillation in vacuo
  4. customAfter separating the phases
  5. extractionthe aqueous phase was extracted a further twice with ether
  6. dry with materialThe combined ether extracts were dried
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was taken up in diisopropyl ether, whereafter crystallization
  10. filtrationThe crystalline substance was filtered off under suction

출처 및 근거

ORD 기록
ord-795c1401c2c24f4abae7174deb3ebc46
출처 데이터셋
uspto-grants-1989_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04818758

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