Sodium Carbonate → HCID 46743463, compound

HRID 1533168Notes

Reaction equation

HRID 1533168 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-9f923f70edc444c3bd812fb34534b97c
Source dataset
uspto-grants-2001_03
Patent number
US06207697B1

Reaction notes

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