Hydrochloric Acid → HCID 22628171, compound

HRID 278622Notes

Reaction equation

HRID 278622 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]3[O:23][CH2:24][O:25][C:19]=3[CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:26]>C(OCC)(=O)C>[ClH:26].[CH2:24]1[O:23][C:20]2[CH:21]=[CH:22][C:17]([S:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)(=[O:16])=[O:15])=[CH:18][C:19]=2[O:25]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22628155HCID 22628155, compound

Product 1

HCID 22628171HCID 22628171, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 1-tert-butoxycarbonyl-4-(3,4-methylenedioxybenzenesulfonyl)piperazine (0.5g) in ethyl acetate (2 ml) was added 4 N HCl in ethyl acetate (10 ml), and the mixture was stirred at room temperature for 30 minutes. The precipitated crystals were filtered to give 3,4-methylenedioxybenzenesulfonylpiperazine hydrochloride (0.39g). To a solution of the crystals (100 mg) in dichloromethane (3 ml) were added triethylamine (0.05 ml), 4-methyl-2-(4-pyridyl)thiazole-5-carboxylic acid (74 mg) and WSC (70 mg), and the mixture was stirred at room temperature for 2 hours and concentrated. To the residue was added water, and the solution was extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and concentrated to give the title compound as crystals (90 mg). The crystals were filtered and washed with ether. NMR (CDCl3): 2.48(3H, s), 3.07(4H, m), 3.75(4H, m), 6.12(2H, s), 6.93(1H, d, J=8.2 Hz), 7.17(2H, s), 7.31(1H, d, J=8.2 Hz), 7.74(2H, d, J=6.2 Hz), 8.71(2H, d, J=6.2 Hz). IR(KBr):1626, 1479, 1427, 1342, 1250 cm1.

Workup

  1. filtrationThe precipitated crystals were filtered

Sources & evidence

ORD record
ord-26544d5a1a0d4b6fbfaf7e4367dc9312
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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