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

HRID 1987902Notes

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-197d328ba2bb4d57a1e768c77e49bc9a
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07553836B2

Reaction notes

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