Tri-tert-butylphosphine tetrafluoroborate → 1-[4-Azetidin-1-yl-2-(4,4-dimethylcyclohexyl)phenyl]-4-butylpiperazine

HRID 32177

반응식

HRID 32177 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:9]2)=[C:4]([CH:18]2[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH2:19]2)[CH:3]=1.Cl.[NH:27]1[CH2:30][CH2:29][CH2:28]1.CC(C)([O-])C.[Na+].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O.C1(C)C(C)=CC=CC=1>[N:27]1([C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:9]3)=[C:4]([CH:18]3[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH2:19]3)[CH:3]=2)[CH2:30][CH2:29][CH2:28]1

참가 물질

9

반응물 4

HCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 12308726Azetidine hydrochlorideHCID 231417381-[4-Bromo-2-(4,4-dimethylcyclohexyl)phenyl]-4-butylpiperazineHCID 23676156Sodium t-butoxide

생성물 1

HCID 597694311-[4-Azetidin-1-yl-2-(4,4-dimethylcyclohexyl)phenyl]-4-butylpiperazine

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 7237O-Xylene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

A mixture of 1-[4-bromo-2-(4,4-dimethylcyclohexyl)phenyl]-4-butylpiperazine (50 mg, 0.123 mmol) produced in Example (57b), azetidine hydrochloride (17 mg, 0.185 mmol), sodium t-butoxide (47 mg, 0.492 mmol), palladium(II) acetate (3 mg, 0.0123 mmol), tri-t-butylphosphonium tetrafluoroborate (11 mg, 0.0369 mmol) and xylene (1 mL) was stirred for 3 hours at an external temperature of 100° C. Water was added to the reaction mixture and extraction was performed with ethyl acetate. The separated organic layer was filtered through Celite. The solvent was distilled off by nitrogen stream to the filtrate. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 1-[4-azetidin-1-yl-2-(4,4-dimethylcyclohexyl)phenyl]-4-butylpiperazine as a colorless solid.

후처리

  1. filtrationThe separated organic layer was filtered through Celite
  2. distillationThe solvent was distilled off by nitrogen stream to the filtrate
  3. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-33f191f7e03346e3b882e7d82f26d813
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425554B2

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