Sodium Carbonate → HCID 46743463, compound

HRID 1267151Notes

Reaction equation

HRID 1267151 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:14]([S:21](Cl)(=[O:23])=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[Na+].[Na+]>CC#N.CCOC(C)=O>[C:1]([N:8]1[CH2:9][CH2:10][N:11]([S:21]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:23])=[O:22])[CH2:12][CH2:13]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 74740Phenylmethanesulfonyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 46743463HCID 46743463, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  1. washwashed with water (50 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0693cbc69c3543789042c466d592132d
Source dataset
uspto-grants-2003_04
Patent number
US06552042B2

Reaction notes

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