1-Chloroethyl chloroformate → Hydrochloric Acid

HRID 251473

反応式

HRID 251473 の反応式
C([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[O:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:23]C(OC(Cl)C)=O>ClCCl>[NH:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[O:14]2)[CH2:10][CH2:9]1.[ClH:23]

参加物

5

反応物 2

HCID 5213051-Chloroethyl chloroformateHCID 102664061'-Benzyl-3H-spiro[isobenzofuran-1,4'-piperidin]-3-one

生成物 2

HCID 313Hydrochloric Acid収率 484%HCID 98342553H-spiro(isobenzofuran-1,4'-piperidin)-3-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

To a solution of 1′-benzyl-3H-spiro[isobenzofuran-1,4′-piperidin]-3-one 1b (6 g, 20.4 mmol) in dichloromethane (30 mL) was added dropwise 1-chloroethyl chloroformate (2.9 g, 20.4 mmol). The mixture was stirred at 25° C. for 5 hr and then was concentrated to dryness under reduced pressure. The residue was dissolved in methanol and the mixture was heated to reflux for 30 min. The mixture was concentrated to dryness and ether was added. The precipitated solid was collected by filtration and washed with ether, dried in air to obtain 3H-spiro[isobenzofuran-1,4′-piperidin]-3-one 1c as its HCl salt (3.6 g). 1H-NMR (400 MHz, DMSO-d6) δ 9.16 (br, 2H), 7.86-7.81 (m, 2H), 7.63 (t, J=7.6 Hz, 1H), 7.56 (d, J=7.2 Hz, 1H), 3.39-3.42 (m, 2H), 3.11-3.14 (m, 2H), 2.47-2.48 (m, 2H), 1.85 (d, J=14.4 Hz, 2H). MS (ESI) m/z (M+H+): 203.24.

後処理

  1. concentrationwas concentrated to dryness under reduced pressure
  2. dissolutionThe residue was dissolved in methanol
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 30 min
  5. concentrationThe mixture was concentrated to dryness and ether
  6. additionwas added
  7. filtrationThe precipitated solid was collected by filtration
  8. washwashed with ether
  9. customdried in air

出典と根拠

ORDレコード
ord-89918feb11fd4c38bf5b490d6eb41b76
出典データセット
uspto-grants-2011_01
特許番号
US07863449B2

関連ノート

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