Chloroacetyl chloride → 2-Chloro-1-{1,4-dioxa-8-azaspiro[4.5]decan-8-yl}ethan-1-one
Reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:18][CH2:19][C:20](Cl)=[O:21]>ClCCl>[Cl:18][CH2:19][C:20]([N:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)=[O:21]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 1,4-dioxa-8-azaspiro[4,5]decane (9.80 g, 67.1 mmol) in dichloromethane (150 mL) under nitrogen was added triethylamine (11.2 mL, 80.5 mmol. This was then cooled to 0° C. and to this was added dropwise with stirring 2-chloroacetyl chloride (6.53 mL, 80.5 mmol) in dichloromethane (50 mL) over 1 and a half hours. This was then stirred overnight warming to room temperature in the process. The reaction was then quenched by adding 1 N HCl (100 mL). This was then extracted with ethyl acetate and the ethyl acetate layers were dried with solid anhydrous magnesium sulfate powder, filtered and concentrated to give 2-Chloro-1-(1,4-dioxa-8-azaspiro[4,5]decan-8-yl)ethan-1-one as a brown oil (15.44 g). This was used without purification for the next step.
Workup
- temperaturewarming to room temperature in the process
- customThe reaction was then quenched
- additionby adding 1 N HCl (100 mL)
- extractionThis was then extracted with ethyl acetate
- dry with materialthe ethyl acetate layers were dried with solid anhydrous magnesium sulfate powder
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4e808dfb818947ce9e5b6078a8805022
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346815B2
Reaction notes
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