Methanesulfonyl chloride → ((2R)-1,4-dibenzyl-2-piperazinyl)methyl methanesulfonate
Reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@@H:9]1[CH2:21][OH:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>C(Cl)Cl>[CH3:32][S:33]([O:22][CH2:21][C@H:9]1[CH2:10][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12][CH2:13][N:8]1[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:35])=[O:34]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
A mixture of (R)-(1,4-dibenzylpiperazin-2-yl)methanol (4.00 g, 13.49 mmol, US2007/0088039) and Hünig's base (2.35 mL, 13.49 mmol) in CH2Cl2 (27 mL) was stirred at 0° C. and methanesulfonyl chloride (1.04 mL, 13.49 mmol) was added drop-wise. The reaction mixture was filtered through a short pad of silica gel, using 19:1 CH2Cl2/Et2O (1000 mL) to rinse. The filtrate was concentrated in vacuo while maintaining the temperature below 25° C. Diethyl ether was added to the residue, the resulting slurry was placed in a sonicator for 1 min, filtered through a fitted funnel and the filtrate was concentrated to give a white solid ((2R)-1,4-dibenzyl-2-piperazinyl)methyl methanesulfonate (4.42 g).
Workup
- filtrationThe reaction mixture was filtered through a short pad of silica gel
- washto rinse
- concentrationThe filtrate was concentrated in vacuo
- temperaturewhile maintaining the temperature below 25° C
- additionDiethyl ether was added to the residue
- filtrationfiltered through a fitted funnel
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-c712bca14f8a45769e83740a3d07432c
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431563B2
Reaction notes
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