Anisole → [1,4]Bipiperidinyl-2-thione

HRID 2221077ノート

反応式

HRID 2221077 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f64ab98eb11f4ff7823caedd4b5c605b
出典データセット
uspto-grants-2008_05
特許番号
US07368461B2

反応ノート

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