Potassium Carbonate → 2-(6-Chloropyridin-3-yl)-3-oxa-1-azaspiro[4.5]dec-1-ene

HRID 251449

反応式

HRID 251449 の反応式
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2([CH2:15][OH:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=O)=[CH:4][N:3]=1.S(Cl)(Cl)=O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]2[O:16][CH2:15][C:9]3([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]3)[N:8]=2)=[CH:17][CH:18]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 119503606-chloro-N-[1-(hydroxymethyl)cyclohexyl]nicotinamide

生成物 1

HCID 119507212-(6-Chloropyridin-3-yl)-3-oxa-1-azaspiro[4.5]dec-1-ene収率 55%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

To a solution of 6-chloro-N-[1-(hydroxymethyl)cyclohexyl]nicotinamide ax47 (2.17 g, 8.06 mmol, 1 eq) in chloroform (80 ml) is added thionyl chloride (1.8 ml, 24.18 mmol, 3 eq). The mixture is stirred at reflux for 2 h 30 before removing the volatiles under vacuum. The residue is dissolved in acetone and treated with potassium carbonate (2 eq), at reflux. After an aqueous work-up, the organic phase is dried over magnesium sulfate and concentrated in vacuo to give 1.86 g of a yellow solid. Purification over silicagel (eluent: dichloromethane/methanol/ammonia 99:1:0.1) finally yields 0.56 g of 2-(6-chloropyridin-3-yl)-3-oxa-1-azaspiro[4.5]dec-1-ene ax49.

後処理

  1. temperatureat reflux for 2 h 30
  2. custombefore removing the volatiles under vacuum
  3. dissolutionThe residue is dissolved in acetone
  4. temperatureat reflux
  5. dry with materialAfter an aqueous work-up, the organic phase is dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f7e4fe3ff9b64a1485d62ca2f11d7cf4
出典データセット
uspto-grants-2011_01
特許番号
US07863450B2

関連ノート

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