Triethylamine → 3-(Benzyloxymethyl)-1-(thiophen-2-ylsulfonyl)piperazine
Reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][NH:14][CH2:13][CH2:12][NH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH:10]1[NH:11][CH2:12][CH2:13][N:14]([S:28]([C:24]2[S:23][CH:27]=[CH:26][CH:25]=2)(=[O:30])=[O:29])[CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
5
Conditions
- Temperature
- 0 °C
Procedure
A 250 mL round-bottomed flask was charged with 2-(benzyloxymethyl)piperazine (2.10 g, 10.1 mmol), triethylamine (1.42 mL, 10.2 mmol) and CH2Cl2 (50 mL). After cooling to 0° C., 2-thiophenesulfonyl chloride (1.84 g, 10.1 mmol, Sigma-Aldrich, St. Louis, Mo.) was added slowly via syringe. After 2 h, the mixture was concentrated and diluted with EtOAc (200 mL). The organic solution was washed with 1 N HCl (2×50 mL) and the combined acidic layers made basic with Na2CO3. The resulting basic solution was extracted with EtOAc (3×100 mL) and the combined organic layers were dried (MgSO4), filtered and concentrated to give 3-(benzyloxymethyl)-1-(thiophen-2-ylsulfonyl)piperazine (1.79 g) as a yellow tar.
Workup
- concentrationthe mixture was concentrated
- additiondiluted with EtOAc (200 mL)
- washThe organic solution was washed with 1 N HCl (2×50 mL)
- extractionThe resulting basic solution was extracted with EtOAc (3×100 mL)
- dry with materialthe combined organic layers were dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-506319d084ba4eaf90179f9f027d5bf4
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431563B2
Reaction notes
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