Sodium Iodide → 1-(3-Fluoropropyl)-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine

HRID 32197

반응식

HRID 32197 반응식
[CH3:1][C:2]1([CH3:22])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH2:3]1.Br[CH2:24][CH2:25][CH2:26][F:27].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>C(OCC)C.CN(C)C=O>[F:27][CH2:26][CH2:25][CH2:24][N:19]1[CH2:18][CH2:17][N:16]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:4]2[CH2:3][C:2]([CH3:22])([CH3:1])[CH2:7][C:6]([CH3:8])([CH3:9])[CH2:5]2)[CH2:21][CH2:20]1

참가 물질

8

반응물 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 67699Propane, 1-bromo-3-fluoro-HCID 516892Sodium BicarbonateHCID 119922841-[2-(3,3,5,5-Tetramethylcyclohexyl)phenyl]piperazine

생성물 1

HCID 231418741-(3-Fluoropropyl)-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

A mixture of 1-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine (30 mg, 0.1 mmol) produced in Example (8b), 1-bromo-3-fluoropropane (18.0 mg, 0.125 mmol), sodium iodide (1.5 mg, 0.01 mmol), potassium carbonate (20.8 mg, 0.15 mmol) and dimethylformamide (1 mL) was stirred for 2 hours at an external temperature of 80° C. Saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture and extraction was performed with diethyl ether. The solvent was distilled off by nitrogen stream to the separated organic layer. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 1-(3-fluoropropyl)-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine.

후처리

  1. distillationThe solvent was distilled off by nitrogen stream to the separated organic layer
  2. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

출처 및 근거

ORD 기록
ord-f89a82df80124415b2f6ab1272ec7910
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425554B2

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