Maleic Acid → 44742-89-4
Reaction equation
C[N:2]([C@H]1C2C(=CC=CC=2)[C@H](C2C=CC(Cl)=C(Cl)C=2)C1)C.[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]\[C:24]([OH:26])=[O:25]>C(O)C>[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]\[C:24]([O-:26])=[O:25].[NH4+:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Trans-1-(N,N-dimethylamino)-3-(3′,4′-dichlorophenyl)indan (13 g, 0.042 mole) was dissolved in ethanol (60 mL) at 50° C. In a separate flask, maleic acid (4.95 g, 0.042 mol) was dissolved in 20 mL of ethanol at 50° C., then added to the solution of trans-1-(N,N-dimethylamino)-3-(3′,4′-dichlorophenyl)indan. The mixture was stirred at 50° C. for 1 h, then at 10° C. for 2 h. The precipitated product was collected by filtration, then washed with cold ethyl acetate (40 mL). The solid was dried under high vacuum to give 13.8 g (77%) of N,N-dimethyl [3-(3′,4′-dichlorophenyl) indan-1-γ1] ammonium hydrogen maleate. The ratio of the undesired cis isomer was 0.3% as detected by HPLC.
Workup
- waitat 10° C. for 2 h
- filtrationThe precipitated product was collected by filtration
- washwashed with cold ethyl acetate (40 mL)
- customThe solid was dried under high vacuum
Sources & evidence
- ORD record
- ord-abff57e2b6554966806ac51e28c7a355
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06268535B1
Reaction notes
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