Triethylamine → 1-Boc-4-(4-Nitrobenzyl)piperazine
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].C(N(CC)CC)C.Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1>CC#N>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of piperazine-1-carboxylic acid tert-butyl ester (1.90 g, 10.2 mmol) and triethylamine (1.55 mL, 11.1 mmol) in CH3CN (9 mL) was treated with 1-bromomethyl-4-nitro-benzene (2.00 g, 9.26 mmol) as a solution in CH3CN (15 mL) at RT for 20 min. The mixture was concentrated in vacuo. The residue was taken up in CH2Cl2 (20 mL) and washed with water (1×20 mL). The aqueous layer was extracted with CH2Cl2 (2×20 mL), and the combined organic layers were washed with water (1×40 mL), dried over MgSO4 and concentrated in vacuo. Purification of the residue on a 50-g Isolute SPE column on a FlashMaster system with 10-25% EtOAc-hexane afforded the title compound (2.82 g, 95%) as a white solid. Mass spectrum (ESI, m/z): Calcd. for C16H23N3O4, 322.2 (M+H). found 321.9.
Workup
- concentrationThe mixture was concentrated in vacuo
- washwashed with water (1×20 mL)
- extractionThe aqueous layer was extracted with CH2Cl2 (2×20 mL)
- washthe combined organic layers were washed with water (1×40 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customPurification of the residue on a 50-g Isolute SPE column on a FlashMaster system with 10-25% EtOAc-hexane
Sources & evidence
- ORD record
- ord-a68bfda39546458d9902d69eba559f20
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08674100B2
Reaction notes
Loading…