1-Chloroethyl chloroformate → 1-[1-(4-Nitrophenyl)piperidin-4-yl]piperazine monohydrochloride

HRID 1526246Notes

Reaction equation

C[N:2]1[CH2:7][CH2:6][N:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH2:4][CH2:3]1.[Cl:23]C(OC(Cl)C)=O>ClCCCl>[ClH:23].[N+:20]([C:17]1[CH:16]=[CH:15][C:14]([N:11]2[CH2:10][CH2:9][CH:8]([N:5]3[CH2:6][CH2:7][NH:2][CH2:3][CH2:4]3)[CH2:13][CH2:12]2)=[CH:19][CH:18]=1)([O-:22])=[O:21]

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 1-methyl-4-[1-(4-nitrophenyl)piperidin-4-yl]piperazine (4.84 g) and 1,2-dichloroethane (50 mL) was added 1-chloroethyl chloroformate (2.2 mL), followed by stirring at 90° C. for 3 hours. The solvent was evaporated under reduced pressure and then methanol (85 mL) was added thereto, followed by heating and refluxing for 1 hour. The solvent was evaporated under reduced pressure and the obtained residue was washed with ethyl acetate to obtain 1-[1-(4-nitrophenyl)piperidin-4-yl]piperazine monohydrochloride (3.74 g) as a yellow solid.

Workup

customThe solvent was evaporated under reduced pressure
additionmethanol (85 mL) was added
temperatureby heating
temperaturerefluxing for 1 hour
customThe solvent was evaporated under reduced pressure
washthe obtained residue was washed with ethyl acetate

Sources & evidence

ORD record: ord-b9d8d4d4d6494150b71f16869f11df99
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085540B2

Reaction notes

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