Methyl 4-fluorobenzoate → Methyl 4-(4-methyl-1,4-diazepan-1-yl)benzoate
Reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.F[C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1>CC(N(C)C)=O>[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)[CH2:4][CH2:3]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
1-Methyl-1,4-diazepane (15.07 g, 132.00 mmol) was added to methyl 4-fluorobenzoate (7.76 mL, 60 mmol) in DMA (150 mL). The resulting solution was stirred at 100° C. for 40 h. The reaction mixture was evaporated and quenched with 2M sodium hydroxide (50 ml). This was extracted with DCM (3×50 ml). The combined organic extracts were washed with saturated brine (50 ml), dried over MgSO4, filtered and evaporated to dryness. The crude product was purified by silica column chromatography, eluting with a gradient of 0 to 10% MeOH in DCM. Pure fractions were evaporated to dryness to afford methyl 4-(4-methyl-1,4-diazepan-1-yl)benzoate (3.59 g, 24.10%) as a tan waxy solid.
Workup
- customThe reaction mixture was evaporated
- customquenched with 2M sodium hydroxide (50 ml)
- extractionThis was extracted with DCM (3×50 ml)
- washThe combined organic extracts were washed with saturated brine (50 ml)
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated to dryness
- customThe crude product was purified by silica column chromatography
- washeluting with a gradient of 0 to 10% MeOH in DCM
- customPure fractions were evaporated to dryness
Sources & evidence
- ORD record
- ord-1f03030c2219419f825a2e9b4cf83a4c
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08604022B2
Reaction notes
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