Pyridine → 1-[(6-Chloronaphthalen-2-yl)sulfonyl]-3-[carbamoylmethyl]piperazine Hydrochloride

HRID 352864Notes

Reaction equation

HRID 352864 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:27])[CH:23]=3)[CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH:9]1[CH2:28][C:29](O)=[O:30])=O)(C)(C)C.[N:32]1C=CC=CC=1.C(=O)(O)[O-].[NH4+].C(=O)(OOC(C)(C)C)OOC(C)(C)C>CN(C)C=O.ClCCl>[ClH:27].[Cl:27][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[C:17]([S:14]([N:11]1[CH2:12][CH2:13][NH:8][CH:9]([CH2:28][C:29](=[O:30])[NH2:32])[CH2:10]1)(=[O:16])=[O:15])[CH:26]=[CH:25]2

Participants

7

Reactant 4

HCID 1049PyridineHCID 14013Ammonium BicarbonateHCID 12432162Bis(1,1-dimethylethyl) carbonodiperoxoateHCID 227100621-Tert-butoxycarbonyl-2-carboxymethyl-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine

Product 1

HCID 227108031-[(6-Chloronaphthalen-2-yl)sulfonyl]-3-[carbamoylmethyl]piperazine Hydrochloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

In N,N-dimethylformamide (20 ml), 1-tert-butoxycarbonyl-2-carboxymethyl-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine (800 mg) was dissolved, followed by the addition of pyridine (0.85 ml), ammonium bicarbonate (417 mg) and di-tert-butoxy carbonate (1.15 g). The resulting mixture was stirred at room temperature for 7 hours. After concentration of the reaction mixture under reduced pressure, the residue was added with dichloromethane, washed with 1N hydrochloric acid and a saturated aqueous solution of sodium bicarbonate, each once and then dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. After the addition of saturated aqueous hydrochloric acid in ethanol (30 ml) to the residue, the resulting mixture was concentrated under reduced pressure. While washing with ethanol, the solid thus precipitated was removed by filtration. The filtrate was then concentrated under reduced pressure. The residue was crystallized in methanol, whereby the title compound (426 mg) was obtained as a colorless solid.

Workup

  1. washwashed with 1N hydrochloric acid
  2. dry with materiala saturated aqueous solution of sodium bicarbonate, each once and then dried over anhydrous sodium sulfate
  3. distillationThe solvent was then distilled off under reduced pressure
  4. additionAfter the addition of saturated aqueous hydrochloric acid in ethanol (30 ml) to the residue
  5. concentrationthe resulting mixture was concentrated under reduced pressure
  6. washWhile washing with ethanol
  7. customthe solid thus precipitated
  8. customwas removed by filtration
  9. concentrationThe filtrate was then concentrated under reduced pressure
  10. customThe residue was crystallized in methanol

Sources & evidence

ORD record
ord-27625cf203a94a049bb325269e23810d
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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