Dimethylamine → N,N-Dimethyl-1,4-dioxaspiro[4.5]decane-6-carboxamide
Reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH:6]2[C:11](Cl)=[O:12])[O:4][CH2:3][CH2:2]1.C1(C)C=CC=CC=1.[CH3:21][NH:22][CH3:23].O>C(OCC)(=O)C>[CH3:21][N:22]([CH3:23])[C:11]([CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C:5]21[O:4][CH2:3][CH2:2][O:1]2)=[O:12]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
To a 1 M solution of 1,4-dioxa-spiro[4.5]decane-6-carbonyl chloride in toluene (1 mL, 1 mmol) was added at 0° C. a 7.9 M solution of dimethylamine in water (1.27 mL, 10 mmol). The mixture was stirred at 20° C. for 1 h, then diluted with ethyl acetate (40 mL), and washed successively with water (10 mL), saturated aqueous sodium carbonate solution (10 mL), 1 N hydrochloric acid, and with brine (10 mL). The organic layer was dried over sodium sulfate and evaporated under reduced pressure to give the title compound (69 mg, 32%) as colorless oil. MS ISP (m/e): 214.3 (100) [(M+H)+].
Workup
- washwashed successively with water (10 mL), saturated aqueous sodium carbonate solution (10 mL), 1 N hydrochloric acid
- dry with materialThe organic layer was dried over sodium sulfate
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-958c3039777049b0bc7e2b9620142f73
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07923450B2
Reaction notes
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