4-(4-(p-Chlorophenyl)-4-hydroxypiperidinyl)-3'-phenylbutyrophenone → Hexane

HRID 1080607

반응식

HRID 1080607 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5](C2(O)CCN(CCCC([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=O)CC2)=[CH:4][CH:3]=1.ClC1C=CC(C2(O)CCN(CCCC(C3C=CC=C(C4C=CC=CC=4)C=3)=O)CC2)=CC=1.C1(C(C2CC2)=O)CC1.C1(C2C=CC=CC=2)C=CC=CC=1.C1(C2C=CC=CC=2)C=CC=CC=1.C1C(C(CCCN2CCC(O)(C3C=CC(Cl)=CC=3)CC2)=O)=CC=C(F)C=1>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[C:20]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:19]=1.[CH3:6][CH2:7][CH2:2][CH2:3][CH2:4][CH3:5]

참가 물질

8

반응물 4

HCID 233649974-(4-(p-Chlorophenyl)-4-hydroxypiperidinyl)-3'-phenylbutyrophenoneHCID 233650054-(4-(p-Chlorophenyl)-4-hydroxypiperidinyl)-2'-phenylbutyrophenoneHCID 67743227Biphenyl cyclopropyl ketoneHCID 86750049Para-biphenyl haloperidol

생성물 2

HCID 7095BiphenylHCID 8058Hexane수율 12%

시약·촉매·용매 2

HCID 7237O-Xylene용매HCID 8857Ethyl Acetate용매

실험 절차

This example describes the synthesis of both 4-(4-(p-chlorophenyl)-4-hydroxypiperidinyl)-2'-phenylbutyrophenone (UCSF51) and 4-(4-(p-chlorophenyl)-4-hydroxypiperidinyl)-3'-phenylbutyrophenone (UCSF52). The ortho and meta biphenyl analogs of halopeddol were prepared from the opening of the cyclopropyl ring of the corresponding biphenyl cyclopropyl ketone (875 mg of the ortho isomer and 500 mg of the meta isomer) by 4-(4 chlorophenyl)4-hydroxy pipeddine by refluxing the two reagents in xylene for 5 days. The reaction was worked up as described for the synthesis of para-biphenyl haloperidol. The products were separated by flash chromatography using a slow gradient from 100% CH2Cl2 to 100% ethyl acetate to 10% methanol in ethyl acetate as eluent. Pooling of the fractions containing product followed by evaporation of the solvent resulted in an orange liquid for the ortho isomer, and a tan solid for the meta. In ethyl acetate, the Rf 's are 0.17 for o-biphenyl haldol, UCSF51, and 0.26 for the meta derivative, UCSF52. Both products were recrystallized from hexane yielding approximately 200 mg (12% yield), and 350 mg (35% yield), of the ortho and meta isomers respectively. A melting point of 96°-97° C. was determined for 4-(4-(p-chlorophenyl)-4-hydroxypiperidinyl)-2'-phenylbutyrophenone, and a melting point of 99°-100° C. was determined for 4-(4-(p-chlorophenyl)-4-hydroxypiperidinyl)-3'-phenylbutyrophenone. Spectral data supported the assigned structures for both products.

후처리

  1. customThe products were separated by flash chromatography
  2. additionPooling of the fractions containing product
  3. customfollowed by evaporation of the solvent
  4. customresulted in an orange liquid for the ortho isomer

출처 및 근거

ORD 기록
ord-1d76d02d05764962b4f13b65a592a53e
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05583000

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