Benzamide → HCID 21940734, compound
Reaction equation
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CN[C@@H:20]1[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]1NC.I/C=C/CCCC>[Cu]I.C1(C)C=CC=CC=1>[CH:25](/[NH:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[CH:20]\[CH2:21][CH2:22][CH2:23][CH3:24]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
A 15 mL resealable Schlenk tube was charged with CuI (9.6 mg, 0.0504 mmol, 5.0 mol %), benzamide (145 mg, 1.20 mmol), K3PO4 (430 mg, 2.03 mmol), evacuated and backfilled with argon. trans-N,N′-Dimethyl-1,2-cyclohexanediamine (16 μL, 0.102 mmol, 10 mol %), trans-1-iodo-1-hexene (143 μL, 1.00 mmol), and toluene (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 25° C. for 24 h. The resulting light blue suspension was allowed to reach room temperature and then filtered through a 0.5×1 cm pad of silica gel eluting with 10 mL of ethyl acetate. The filtrate was concentrated, the residue was dissolved in 5 mL of dichloromethane and purified by flash chromatography on silica gel (2×15 cm, hexane-ethyl acetate, 15 mL fractions). Fractions 12–19 provided 140 mg (69% yield) of the desired product as white needles.
Workup
- customevacuated
- customThe Schlenk tube was sealed with a Teflon valve
- customto reach room temperature
- filtrationfiltered through a 0.5×1 cm pad of silica gel eluting with 10 mL of ethyl acetate
- concentrationThe filtrate was concentrated
- dissolutionthe residue was dissolved in 5 mL of dichloromethane
- custompurified by flash chromatography on silica gel (2×15 cm, hexane-ethyl acetate, 15 mL fractions)
Sources & evidence
- ORD record
- ord-0aa10050af4d4998a52a049182e36177
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115784B2
Reaction notes
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