Triethylamine → Tert-butyl 4-(cyclopropylmethyl)piperazine-1-carboxylate
Reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:15][CH:16]1[CH2:18][CH2:17]1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH:16]1([CH2:15][N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)[CH2:18][CH2:17]1Participants
Procedure
Tert-butyl piperazine-1-carboxylate 7a (6.14 g, 33 mmol), bromomethyl-cyclopropane (4.05 g, 30 mmol) and triethylamine (6.06 g, 60 mmol) were dissolved in 70 mL of dichloromethane. The reaction solution was stirred for 12 hours. The resulting solution was added with 50 mL of aqeuous saturated sodium bicarbonate solution and extracted with dichloromethane (50 mL×3). The combined organic phase was washed with saturated sodium chloride solution (50 mL), dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound tert-butyl 4-(cyclopropylmethyl)piperazine-1-carboxylate 31a (4.50 g, yield: 62.5%) as a yellow oil.
Workup
- extractionextracted with dichloromethane (50 mL×3)
- washThe combined organic phase was washed with saturated sodium chloride solution (50 mL)
- dry with materialdried over anhydrous magnesium sulfate
- concentrationThe filtrate was concentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-a4e7fcf06ce94149969077785e235f67
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691822B2
Reaction notes
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