Anisole → [1,4]Bipiperidinyl-2-thione

HRID 2221077노트

반응식

HRID 2221077 반응식
C1(OC)C=CC=CC=1.C(OC([N:19]1[CH2:24][CH2:23][CH:22]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][C:26]2=[S:31])[CH2:21][CH2:20]1)=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl.CO>[N:25]1([CH:22]2[CH2:23][CH2:24][NH:19][CH2:20][CH2:21]2)[CH2:30][CH2:29][CH2:28][CH2:27][C:26]1=[S:31]

참가 물질

7

반응물 4

HCID 7519AnisoleHCID 11430Potassium CarbonateHCID 24436Sodium SulfateHCID 233699572-Thioxo-[1,4']bipiperidinyl-1'-carboxylic acid benzyl ester

생성물 1

HCID 23369948[1,4]Bipiperidinyl-2-thione

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

Anisole (2.5 mL) was added to a solution of 2-thioxo-[1,4′]bipiperidinyl-1′-carboxylic acid benzyl ester (2.4 g) in methylene chloride (40 mL) at 0° C. followed by the addition of trifluorosulfonic acid (3.4 mL). After 30 minutes, solid potassium carbonate was added, then sodium sulfate and methanol. The solids were removed by filtration and the filtrate was concentrated. The residue was dissolved in methanol and neutralized by passage through a column of Amberlyst A-21 (slightly basic) resin. The filtrate was collected and concentrated and purified by chromatography, with methylene chloride:methanol (gradient 95:5, 90:10) as eluent. The title compound was obtained as a white solid (0.93 g). MS: m/z=199 (M+H).

후처리

  1. customThe solids were removed by filtration
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in methanol
  4. customThe filtrate was collected
  5. concentrationconcentrated
  6. custompurified by chromatography, with methylene chloride

출처 및 근거

ORD 기록
ord-f64ab98eb11f4ff7823caedd4b5c605b
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07368461B2

반응 노트

불러오는 중…