N,N-bis(trimethylsilyl)-3-bromo-1-propylamine → HCID 67079576, compound
Reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[CH3:13][Si:14]([CH3:25])([CH3:24])[N:15]([CH2:20][CH2:21][CH2:22]Br)[Si:16]([CH3:19])([CH3:18])[CH3:17]>CN(C)C=O>[CH3:19][Si:16]([N:15]([Si:14]([CH3:13])([CH3:24])[CH3:25])[CH2:20][CH2:21][CH2:22][N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6])([CH3:17])[CH3:18]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
About 4.60 g of potassium phthalimide, 6.37 g of N,N-bis(trimethylsilyl)-3-bromo-1-propylamine, and 15 mL of N,N-dimethylformamide were mixed in a flask. The mixture was stirred for 6 hour while the flask was kept in an oil bath maintained at 80° C. The N,N-dimethylformamide was removed under vacuum. The residue was extracted with 90 mL of cyclohexane and filtered. The filtrate was evaporated under vacuum. The residue was triturated with 80 mL of hexane, cooled with dry ice, and then filtered to give N-[3-bis(trimethylsilyl)amino-1-propyl]phthalimide (BTMSAPPI) as a white solid (5.95 g, 76% yield). 1H NMR data (C6D6, 25° C., referenced to tetramethylsilane) of the product: δ 7.41 (multiplet, 2H, aromatic protons), 6.85 (multiplet, 2H, aromatic protons), 3.44 (triplet, J=7.1 Hz, 2H, CH2 protons), 2.81 (multiplet, 2H, CH2 protons), 1.75 (multiplet, 2H, CH2 protons), 0.06 (singlet, 18H, Si—CH3 protons).
Workup
- customwas kept in an oil bath
- customThe N,N-dimethylformamide was removed under vacuum
- extractionThe residue was extracted with 90 mL of cyclohexane
- filtrationfiltered
- customThe filtrate was evaporated under vacuum
- customThe residue was triturated with 80 mL of hexane
- temperaturecooled with dry ice
- filtrationfiltered
Sources & evidence
- ORD record
- ord-fa3804908a0e420586846297aaacb612
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07906592B2
Reaction notes
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