Triphenylphosphine → 4-[4-[2-(1-methyl-1H-pyrazol-5-yl)ethoxy]phenyl]piperidine

HRID 1675146

반응식

HRID 1675146 반응식
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[NH:15]1[CH2:20][CH2:19][CH:18]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)[CH2:17][CH2:16]1.[CH3:28][N:29]1[C:33]([CH2:34][CH2:35]O)=[CH:32][CH:31]=[N:30]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH3:28][N:29]1[C:33]([CH2:34][CH2:35][O:27][C:24]2[CH:23]=[CH:22][C:21]([CH:18]3[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]3)=[CH:26][CH:25]=2)=[CH:32][CH:31]=[N:30]1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 105115114-Piperidin-4-ylphenolHCID 218324192-(1-methyl-1H-pyrazol-5-yl)ethan-1-ol2회

생성물 1

HCID 673403084-[4-[2-(1-methyl-1H-pyrazol-5-yl)ethoxy]phenyl]piperidine수율 99.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
22 °C

실험 절차

DIAD (64.8 μl, 0.33 mmol) was added to 4-(piperidin-4-yl)phenol (CAS 263139-27-1, 53 mg, 0.30 mmol), 2-(1-methyl-1H-pyrazol-5-yl)ethanol (obtained as described in PCT Int. Appl. WO 2007017222, Intermediate 1) (37.7 mg, 0.30 mmol) and triphenylphosphine (86 mg, 0.33 mmol) in DCM (3 mL) at 20° C. under nitrogen. The resulting mixture was stirred at 22° C. for 3 days. The reaction mixture was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M ammonia in methanol and pure fractions were evaporated to dryness to afford 4-[4-[2-(1-methyl-1H-pyrazol-5-yl)ethoxy]phenyl]piperidine (85 mg, 96%) as a yellow oil.

후처리

  1. customThe reaction mixture was purified by ion exchange chromatography
  2. washThe desired product was eluted from the column
  3. customwere evaporated to dryness

출처 및 근거

ORD 기록
ord-64bc66898c944875a16910785de0ea9b
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003649B2

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