1-Isopropylpiperazine → HCID 86721995, compound
Reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.ClC(Cl)(O[C:19](=[O:25])OC(Cl)(Cl)Cl)Cl.[CH:27]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)([CH3:29])[CH3:28]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:27]([N:30]1[CH2:35][CH2:34][N:33]([C:19]([O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)=[O:25])[CH2:32][CH2:31]1)([CH3:29])[CH3:28]Participants
6
Procedure
To a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (4.4 g, 21.9 mmol) in DCM (100 mL) was carefully added DMAP (5.3 g, 43.8 mmol) and triphosgene (3.2 g, 10.95 mmol) portionwise. After stirring at rt for 2 h, 1-isopropylpiperazine (3.3 g, 26 mmol) was added and the reaction mixture was stirred at rt for 5 h. The reaction was quenched with saturated NH4Cl (100 mL) solution and the mixture was extracted with DCM (3×100 mL). The combined organic layers were washed with saturated NH4Cl (2×100 mL) and brine (50 mL) sequentially, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the title compound as a white solid (7.7 g, 99%). [LCMS: Rt=1.67 min, m/z 356.3 (M+H)+].
Workup
- stirringthe reaction mixture was stirred at rt for 5 h
- customThe reaction was quenched with saturated NH4Cl (100 mL) solution
- extractionthe mixture was extracted with DCM (3×100 mL)
- washThe combined organic layers were washed with saturated NH4Cl (2×100 mL) and brine (50 mL) sequentially
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-6647176f52df4ed9844ddb277c05200b
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273026B2
Reaction notes
Loading…