Sodium Iodide → HCID 23133283, compound
Reaction equation
[C:1]1([CH3:8])[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[Cl:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:31][CH2:30][C:29]2[C:32]3[CH:22]1[CH2:23][CH2:24][C:25]=3[CH:26]=[CH:27][CH:28]=2>CN(C=O)C>[ClH:17].[ClH:17].[CH2:24]1[C:25]2=[C:32]3[C:29](=[CH:28][CH:27]=[CH:26]2)[CH2:30][CH2:31][N:21]([CH2:20][CH2:19][CH2:18][NH:7][C:3]2[CH:2]=[C:1]([CH3:8])[CH:6]=[CH:5][CH:4]=2)[CH:22]3[CH2:23]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of m-tolylamine (21.7 mg, 0.20 mmol) in dry DMF (2 ml) was added K2CO3 (31 mg, 0.22 mmol), NaI (33 mg, 0.22 mmol) and 3-(3-Chloro-propyl)-1,2,2a,3,4,5-hexahydro-3-aza-acenaphthylene (50 mg, 0.21 mmol) and the mixture was stirred overnight at 90° C. The mixture was vacuum concentrated and the residue was dissolved in water (5 mL), extracted with ethyl acetate (3×5 mL) and washed with water. The organic layer was dried and evaporated. The residue was dissolved in ethyl acetate (1 ml) and 2.8 N hydrochloric acid was added. A light brown solid precipitate, which was collected by filtration to give the desired product (40 mg, 66% yield).
Workup
- concentrationconcentrated
- dissolutionthe residue was dissolved in water (5 mL)
- extractionextracted with ethyl acetate (3×5 mL)
- washwashed with water
- customThe organic layer was dried
- customevaporated
- dissolutionThe residue was dissolved in ethyl acetate (1 ml)
- addition2.8 N hydrochloric acid was added
- filtrationA light brown solid precipitate, which was collected by filtration
Sources & evidence
- ORD record
- ord-b5e27b4576a242c09422bbfbfead0b35
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07662862B2
Reaction notes
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