Water → 2-Phenyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole
Reaction equation
Cl.[NH:2]=[C:3]1[CH2:7][CH2:6][CH2:5][NH:4]1.Br[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O.C([O-])([O-])=O.[Na+].[Na+].O>CN(C=O)C>[C:12]1([C:10]2[N:2]=[C:3]3[CH2:7][CH2:6][CH2:5][N:4]3[CH:9]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Prepare 2-iminopyrrolidine hydrochloride (6.98 g, 57.8 mmol) according to Callahan, et al., J. Med. Chem. 2002, 45, 999-1001) and combine 2-bromoacetophenone (3.8 g, 19.3 mmol) with Na2CO3 (8.2 g, 77.2 mmol) in dry DMF (25 mL) and heat at 80° C. for 18 hours. Then, cool the mixture to room temperature, add water (60 mL), and extract with EtOAc (3×100 mL). Concentrate the combined organic layers in vacuo, dilute the residue with ether (100 mL), and wash with cooled water (3×80 mL). Concentrate the organic layer in vacuo to give a white solid, 3.2 g, 89% yield. MS(ES+): m/z=185.1 (M+H)+
Workup
- temperatureThen, cool the mixture to room temperature
- extractionextract with EtOAc (3×100 mL)
- concentrationConcentrate the combined organic layers in vacuo
- additiondilute the residue with ether (100 mL)
- washwash with cooled water (3×80 mL)
- concentrationConcentrate the organic layer in vacuo
- customto give a white solid, 3.2 g, 89% yield
Sources & evidence
- ORD record
- ord-46c20bc4b0b141778ed167ba2058424c
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07320995B2
Reaction notes
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