2-Chloroethyl chloroformate → 5-chloro-3H-spiro[isobenzofuran-1,4'-piperidine]

HRID 270093ノート

反応式

HRID 270093 の反応式
C([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=3[CH2:15][O:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OCCCl)=O>ClCCl>[Cl:22][C:20]1[CH:19]=[CH:18][C:17]2[C:11]3([O:14][CH2:15][C:16]=2[CH:21]=1)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3

参加物

4

反応物 2

HCID 123052-Chloroethyl chloroformateHCID 598336321'-Benzyl-5-chloro-3H-spiro[isobenzofuran-1,4'-piperidine]

生成物 1

HCID 186757315-chloro-3H-spiro[isobenzofuran-1,4'-piperidine]収率 44.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 1′-benzyl-5-chloro-3H-spiro[2-benzofuran-1,4′-piperidine] (950 mg, 3.02 mmol) in dichloromethane (CH2Cl2) (6 mL) was added chloroethyl chloroformate (560.6 mg, 3.92 mmol) slowly at 0° C. After addition was complete the reaction mixture was kept on stirring at 0° C. for 25 min. The volatiles were removed in vacuo, the residue was dissolved in methanol (6 mL) and kept at reflux for 40 min. The volatiles were removed in vacuo and the residue was purified by silica gel flash chromatography (0-5% methanol in dichloromethane, 0.2% ammonium hydroxide, NH4OH) to give the titled compound (300 mg) and 1′-benzyl-5-chloro-3H-spiro[2-benzofuran-1,4′-piperidin] was recovered (320 mg).

後処理

  1. additionAfter addition
  2. customThe volatiles were removed in vacuo
  3. dissolutionthe residue was dissolved in methanol (6 mL)
  4. temperatureat reflux for 40 min
  5. customThe volatiles were removed in vacuo
  6. customthe residue was purified by silica gel flash chromatography (0-5% methanol in dichloromethane, 0.2% ammonium hydroxide, NH4OH)

出典と根拠

ORDレコード
ord-cc8c3d7a9e344659a9abc57f9104ba2f
出典データセット
uspto-grants-2008_11
特許番号
US07449475B2

反応ノート

読み込み中…