1-Chloroethyl chloroformate → Hydrochloric Acid

HRID 251473

Reaction equation

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]

Participants

Conditions

Temperature: 25 °C

Procedure

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.

Workup

concentrationwas concentrated to dryness under reduced pressure
dissolutionThe residue was dissolved in methanol
temperaturethe mixture was heated
temperatureto reflux for 30 min
concentrationThe mixture was concentrated to dryness and ether
additionwas added
filtrationThe precipitated solid was collected by filtration
washwashed with ether
customdried in air

Sources & evidence

ORD record: ord-89918feb11fd4c38bf5b490d6eb41b76
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863449B2

Linked notes

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