Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Phenylmethanesulfonyl chloride | HCID 74740 | — |
| Reactant | tert-Butyl piperazine-1-carboxylate | HCID 143452 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 46743463 | HCID 46743463 | 98% |
Reaction Steps
Acylation of N-Boc-piperazine (1.86 g, 10 mmoL) with benzylsulfonyl chloride (1.9 g, 10 mmol) in CH3CN (20 mL) in the presence of Na2CO3 (1.01 g, 12 mmol) was carried out at rt for 16 hours. The mixture was diluted with EtOAc (150 mL), washed with water (50 mL), dried over MgSO4, and concentrated to give 1N-Boc-4N-benzylsulfonyl-piperazine (3.3 g, 98%). 1H NMR (CDCl3) δ 7.39 (bs, 5H), 4.23 (s, 2H), 3.38-3.35 (m, 4H), 3.07-3.05 (m, 4H), 1.44 (s, 9H). The Boc-intermediate was deprotected with 4M HCl in dioxane (20 mL) at rt for 1 hour. The mixture was diluted with EtOAc, washed with 1N NaOH and water, dried over MgSO4, and concentrated to give the product (1.9 g, 81%). 1H NMR (CDCl3) δ 7.46-7.43 (bs, 5H), 4.22 (s, 2H), 3.11-3.08 (m, 4H), 2.83-2.79 (m, 4H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06552042B2 |
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| Source dataset | uspto-grants-2003_04 |
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| ORD ID | ord-0693cbc69c3543789042c466d592132d |
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| Source note | uspto-grants-2003_04 |
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