Potassium Phosphate, Tribasic → (R)-1-butyl-4-[2-(4,4-dimethylcyclohexyl)-4-(3-methoxypiperidin-1-yl)phenyl]piperazine

HRID 32161

반응식

HRID 32161 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.[CH3:27][O:28][C@@H:29]1[CH2:34][CH2:33][CH2:32][NH:31][CH2:30]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].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.C1(C)C(C)=CC=CC=1>[CH2:14]([N:11]1[CH2:12][CH2:13][N:8]([C:5]2[CH:6]=[CH:7][C:2]([N:31]3[CH2:32][CH2:33][CH2:34][C@@H:29]([O:28][CH3:27])[CH2:30]3)=[CH:3][C:4]=2[CH:18]2[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH2:19]2)[CH2:9][CH2:10]1)[CH2:15][CH2:16][CH3:17]

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 231417381-[4-Bromo-2-(4,4-dimethylcyclohexyl)phenyl]-4-butylpiperazineHCID 69216666(3R)-3-methoxypiperidine hydrochloride

생성물 1

HCID 59769385(R)-1-butyl-4-[2-(4,4-dimethylcyclohexyl)-4-(3-methoxypiperidin-1-yl)phenyl]piperazine수율 59.2%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 7237O-Xylene용매

반응 조건

온도
100 °C

실험 절차

A mixture of 1-[4-bromo-2-(4,4-dimethylcyclohexyl)phenyl]-4-butylpiperazine (37.4 mg, 0.0918 mmol) produced in Example (21c), (R)-3-methoxypiperidine hydrochloride (16.7 mg, 0.110 mmol) produced in Example (49a), tripotassium phosphate (170 mg, 0.801 mmol), palladium(II) acetate (8.2 mg, 0.0365 mmol), tri-t-butylphosphonium tetrafluoroborate (32 mg, 0.110 mmol) and xylene (1.5 mL) was stirred for 4 hours and 30 minutes at an external temperature of 100° C. under a nitrogen atmosphere. The mixture was air-cooled to room temperature and then purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 24 mg of (R)-1-butyl-4-[2-(4,4-dimethylcyclohexyl)-4-(3-methoxypiperidin-1-yl)phenyl]piperazine as a colorless oil.

후처리

  1. temperatureThe mixture was air-cooled to room temperature
  2. custompurified by NH silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-1059d9599d9f45f89d302d12e19044cb
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425554B2

연결된 노트

불러오는 중…