2,2,2-Trichloroethyl chloroformate → HCID 18001190, compound

HRID 478195Notes

Reaction equation

C[N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.Cl[C:35]([O:37][CH2:38][C:39]([Cl:42])([Cl:41])[Cl:40])=[O:36]>ClCCCl>[C:8]1([CH:5]2[CH2:6][CH2:7][N:2]([C:35]([O:37][CH2:38][C:39]([Cl:42])([Cl:41])[Cl:40])=[O:36])[CH2:3][CH2:4]2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 115 °C

Procedure

To a solution of 1-methyl-4-(1-naphthyl)piperidine (0.5 g, 2.2 mmol) in 1,2-dichloroethane (30 mL) was added a proton sponge (2.1 g, 9.9 mmol) and trichloroethyl chloroformate (0.93 mL, 6.6 mmol), and the resulting mixture was stirred at 115° C. overnight. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate, and the ethyl acetate layer was washed with 1 N hydrochloric acid and subsequently with a saturated aqueous sodium chloride. After drying over anhydrous sodium sulfate, the ethyl acetate layer was concentrated, and the resulting crude product was purified by column chromatography on a silica gel (eluent; hexane:ethyl acetate=6:1) to afford the title compound (0.85 g, yield: 100%) as a yellow oil.

Workup

temperatureAfter cooling to room temperature
extractionthe reaction mixture was extracted with ethyl acetate
washthe ethyl acetate layer was washed with 1 N hydrochloric acid and subsequently with a saturated aqueous sodium chloride
dry with materialAfter drying over anhydrous sodium sulfate
concentrationthe ethyl acetate layer was concentrated
customthe resulting crude product was purified by column chromatography on a silica gel (eluent; hexane:ethyl acetate=6:1)

Sources & evidence

ORD record: ord-49f14e5869774bf7ac530ed407076fc4
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06642228B1

Reaction notes

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