1-Chloroethyl chloroformate → Hydrochloric Acid

HRID 251473

반응식

HRID 251473 반응식
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]

참가 물질

5

반응물 2

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

생성물 2

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-89918feb11fd4c38bf5b490d6eb41b76
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863449B2

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