Cesium carbonate → 1-[2-(2-chloro-4-nitrophenoxy)ethyl]Pyrrolidine

HRID 2420708Notes

Reaction equation

C([O-])([O-])=O.[Cs+].[Cs+].Cl.Cl[CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.[Cl:16][C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1[OH:26]>CN(C=O)C>[Cl:16][C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1[O:26][CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of Cs2CO3 (23.1 g, 71.0 mmol), 1-(2-chloroethyl)pyrrolidine, hydrochloride (9.0 g, 53.2 mmol) and 2-chloro-4-nitrophenol (3.0 g, 17.8 mmol) in DMF (50 mL) was heated at 80° C. for 4 days. After dilution with H2O (50 mL), the mixture was extracted with EtOAc (2×100 mL). The combined organic layers were washed with H2O (30 mL), then with brine prior to drying over MgSO4. After removal of the solvent under vacuum, the residue was chromatographed on silica gel using 5%-10% gradient MeOH/CH2Cl2 to yield yellow brownish solid (1.5 g, 31%) MS (ESI) 271 (M+H)+.

Workup

extractionAfter dilution with H2O (50 mL), the mixture was extracted with EtOAc (2×100 mL)
washThe combined organic layers were washed with H2O (30 mL)
dry with materialwith brine prior to drying over MgSO4
customAfter removal of the solvent under vacuum
customthe residue was chromatographed on silica gel using 5%-10% gradient MeOH/CH2Cl2

Sources & evidence

ORD record: ord-4b6afdf5b4c944fdbf2b8f348b1ed003
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07956049B2

Reaction notes

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