1-Chloroethyl chloroformate → Pyridine, 1,2,3,6-tetrahydro-4-[4-(trifluoromethyl)phenyl]-

HRID 2110118Notes

Reaction equation

C([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)=O)C>C1COCC1>[F:23][C:20]([F:21])([F:22])[C:17]1[CH:16]=[CH:15][C:14]([C:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: -20 °C

Procedure

1-Benzyl-4-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydro-pyridine was dissolved in THF (10 mL). The reaction was cooled to −20° C. and 1-chloroethylchloroformate (0.5 mL) in THF (2 ml) was added. The reaction was stirred at −10° C. for 3 h and then concentrated. MeOH (10 mL) was added to the crude mixture and refluxed for 2 h. The solvent was removed to provide 4-(4-trifluoromethyl-phenyl)-1,2,3,6-tetrahydro-pyridine (HCl) which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 9.40 (s, 2H), 7.74 (m, 4H), 6.39 (m, 1H), 3.79 (m, 2H), 3.33 (m, 2H), 2.74 (m, 2H).

Workup

concentrationconcentrated
additionMeOH (10 mL) was added to the crude mixture
temperaturerefluxed for 2 h
customThe solvent was removed

Sources & evidence

ORD record: ord-c27fc3592deb49b8b980dbebc86dc08a
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517884B2

Reaction notes

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