Potassium Carbonate → N-Methyl-N-(2-propynyl)-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarboxamide
Reaction equation
Cl[C:2]([N:4]1[CH2:7][CH:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[CH2:5]1)=[O:3].C(=O)([O-])[O-].[K+].[K+].[CH3:25][NH:26][CH2:27][C:28]#[CH:29]>O1CCCC1>[CH3:25][N:26]([CH2:27][C:28]#[CH:29])[C:2]([N:4]1[CH2:7][CH:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[CH2:5]1)=[O:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
A mixture of 5.6 g (0.02 mole) of 1-chlorocarbonyl-3-[3-(trifluoromethyl)phenoxy]azetidine and 3 g (0.022 mole) of potassium carbonate in 50 ml of tetrahydrofuran was treated while stirring with 1.52 g of N-methylpropargylamine. After stirring for 15 min, 10 g of ice was added and stirring continued for an additional 72 hr. The tetrahydrofuran was decanted from the salt paste and concentrated on a rotary evaporator to yield an amber oil, 5.9 g. This oil solidified when cooled to -70° C. and was recrystallized from hexane to yield 4.6 g (74.2%) of fine white crystals, m.p. 71°-73° C.
Workup
- additionwas treated
- stirringstirring
- waitcontinued for an additional 72 hr
- customThe tetrahydrofuran was decanted from the salt paste
- concentrationconcentrated on a rotary evaporator
- customto yield an amber oil, 5.9 g
- customwas recrystallized from hexane
Sources & evidence
- ORD record
- ord-395a548686c04015babac2957fa75ced
- Source dataset
- uspto-grants-1992_09
- Patent number
- US05151418
Reaction notes
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