Pyridine → Tert-butyl 4-(chlorocarbonyl)piperazine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[Cl:20][C:21](Cl)([O:23]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:21]([Cl:20])=[O:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of piperazine-1-carboxylic acid tert-butyl ester (4.0 g, 22 mmol) in methylene chloride (40 mL) at 0° C. was treated with pyridine (2.65 ml, 33 mmol) and triphosgene (3.2 g, 10.8 mmol). The resulting yellow solution was stirred at 25° C. for 1 h. At this time, the reaction mixture was partitioned between methylene chloride (200 mL) and a 1N aqueous hydrochloric acid solution (75 mL). The organics were dried over magnesium sulfate and concentrated in vacuo to afford 4-chlorocarbonyl-piperazine-1-carboxylic acid tert-butyl ester (4.73 g, 89%) as a yellow solid. This material was used in the next step without further purification
Workup
- customAt this time, the reaction mixture was partitioned between methylene chloride (200 mL)
- dry with materialThe organics were dried over magnesium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-31661f941c814d5b936f21c71da815b1
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07947692B2
Reaction notes
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