Hydrochloric Acid → 958852-64-7
Reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[CH2:5]1[C:9]2([CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH2:8][CH2:7][CH2:6]1.C(N(CC)CC)C.Cl>ClC(Cl)C>[CH2:8]1[C:9]2([CH2:14][CH2:13][N:12]([C:1]([Cl:4])=[O:2])[CH2:11][CH2:10]2)[CH2:5][CH2:6][CH2:7]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
1.57 ml of phosgene (20% solution in toluene, 2.96 mmol) were initially charged in 5 ml of dichloroethane and cooled to −20° C., then a mixture of 8-azaspiro-[4,5]decane (750 mg, 2.96 mmol) and triethylamine (1.28 ml, 9.2 mmol, 3.1 eq.) was added slowly. After 30 min, the mixture was allowed to come to RT; after 1 h, according to LC-MS, a little starting material was still present but also three new peaks. Subsequently, the mixture was added to 2 N aqueous HCl, the aqueous phase was extracted with dichloromethane, and the organic phase was washed with saturated NaHCO3 solution and dried over sodium sulfate; subsequently, the mixture was concentrated by rotary evaporation under reduced pressure. Crude yield: 592 mg
Workup
- additionwas added slowly
- customto come to RT
- waitafter 1 h
- extractionthe aqueous phase was extracted with dichloromethane
- washthe organic phase was washed with saturated NaHCO3 solution
- dry with materialdried over sodium sulfate
- concentrationsubsequently, the mixture was concentrated by rotary evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-0c5effe238c1428d8fd3bdff821460cd
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609681B2
Reaction notes
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