rel-(2R,6S)-2,6-dimethylpiperazine → 2-Ethoxy-5-(cis-2,6-dimethypiperazin-4-ylsulphonyl) benzoic acid

HRID 1061563Notes

Reaction equation

HRID 1061563 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][C@@H:4]([CH3:8])[NH:3]1.Cl[S:10]([C:13]1[CH:14]=[CH:15][C:16]([O:22][CH2:23][CH3:24])=[C:17]([CH:21]=1)[C:18]([OH:20])=[O:19])(=[O:12])=[O:11]>O>[CH2:23]([O:22][C:16]1[CH:15]=[CH:14][C:13]([S:10]([N:6]2[CH2:5][C@@H:4]([CH3:8])[NH:3][C@@H:2]([CH3:1])[CH2:7]2)(=[O:12])=[O:11])=[CH:21][C:17]=1[C:18]([OH:20])=[O:19])[CH3:24]

Participants

4

Reactant 2

HCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 113800715-(Chlorosulfonyl)-2-ethoxybenzoic acid

Product 1

HCID 112678772-Ethoxy-5-(cis-2,6-dimethypiperazin-4-ylsulphonyl) benzoic acidYield 70.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 250 ml three-neck flask, 52.6 g (0.23 mol) of cis-2,6-dimethylpiperazine was added to the suspension of compound (II) (53 g, 0.20 mol) in water (170 ml) at about 10° C. with stirring, at the same time the temperature of reacting mixture was kept below 20° C. The reaction was then stirred at 10° C. for another 2 hours. The precipitate was filtered, ice-water washed, dried, and refluxed in acetone for 1 hour, and purified, gave 48 g compound (III) (yield 70%) as white crystalline, m.p. 260.5-273.0° C. (Dec.). HNMR(DMSO) δ: 7.72-7.75(2H, H-4 and H-6 on benzene ring), 7.26-7.28(1H, H-3 on benzene ring), 4.12-4.17(2H, —CH2— on —OCH2CH3), 3.5-3.53(2H, —CH2— on piperazine ring), 2.89-2.92(2H, —CH— on piperazine ring), 1.80-1.86(2H, —CH2— on piperazine ring), 1.31-1.34(3H, —CH3 on —OCH2CH3), 1.0-1.04(6H, two —CH3 groups on piperazine ring).

Workup

  1. customwas kept below 20° C
  2. stirringThe reaction was then stirred at 10° C. for another 2 hours
  3. filtrationThe precipitate was filtered
  4. washice-water washed
  5. customdried
  6. temperaturerefluxed in acetone for 1 hour
  7. custompurified

Sources & evidence

ORD record
ord-d9844571a7a44163a589a03d2a2a5139
Source dataset
uspto-grants-2005_11
Patent number
US06960592B2

Reaction notes

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