Piperazine-2-carboxylic acid → 3((+/-)-2-Carboxypiperazin-4-yl)-propane-1-sulphonic acid

HRID 1609171Notes

Reaction equation

HRID 1609171 reaction equation
Br[CH2:2][CH2:3][CH2:4][S:5]([O-:8])(=[O:7])=[O:6].[Na+].[NH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH:11]1[C:16]([OH:18])=[O:17]>[OH-].[Na+]>[C:16]([CH:11]1[CH2:12][N:13]([CH2:2][CH2:3][CH2:4][S:5]([OH:8])(=[O:7])=[O:6])[CH2:14][CH2:15][NH:10]1)([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 2723758Piperazine-2-carboxylic acidHCID 236790563-bromopropanesulfonic acid sodium salt

Product 1

HCID 134918533((+/-)-2-Carboxypiperazin-4-yl)-propane-1-sulphonic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Sodium 3-bromo-propane-1-sulphonate (2.25 g, 0.01 mole) was added to a solution of piperazine-2-carboxylic acid (1.3 g, 0.01 mole) in aqueous sodium hydroxide (0.9 g NaOH/30 ml H2O). The resulting solution was maintained at 60°-65° for 12 h. The product, 3((±)-2-carboxypiperazin-4-yl)-propane-1-sulphonic acid, was isolated by passage of the reaction mixture through Dowex-AG-1-acetate resin. Evaporation of the column filtrate and aqueous washings and recrystallization of the crude product from a 50% aqueous ethanol solution yielded 3-((±)-2-carboxy-piperazin-4-yl)-propane-1-sulphonic acid (500 mg) as a white crystalline solid, m.p. 190°-191°.

Workup

  1. temperatureThe resulting solution was maintained at 60°-65° for 12 h

Sources & evidence

ORD record
ord-e1d0ce9f48ba4429b0a96c91216ace5f
Source dataset
uspto-grants-1995_03
Patent number
US05399693

Reaction notes

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