Cysteamine Hydrochloride → 2-{2-[2-(4-Phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine

HRID 1789374Notes

Reaction equation

HRID 1789374 reaction equation
[OH-].[Na+].Cl.[NH2:4][CH2:5][CH2:6][SH:7].[C:8]1([N:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][O:22][C:23]3[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=3[CH:25]=O)[CH2:16][CH2:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(O)C>[C:8]1([N:14]2[CH2:15][CH2:16][N:17]([CH2:20][CH2:21][O:22][C:23]3[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=3[CH:25]3[NH:4][CH2:5][CH2:6][S:7]3)[CH2:18][CH2:19]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 14798Sodium HydroxideHCID 138089772-[2-(4-Phenylpiperazin-1-yl)ethyloxy]benzaldehyde

Product 1

HCID 137680992-{2-[2-(4-Phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidineYield 91.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2.21 g of sodium hydroxide are added to a solution of 5.75 g of cysteamine hydrochloride in 200 ml of ethanol, and a solution of 14.28 g of 2-[2-(4-phenylpiperazin-1-yl)ethyloxy]benzaldehyde in 100 ml of ethanol is added thereto. After the mixture is stirred at room temperature for 2 hours, the mixture is concentrated under reduced pressure to remove solvent. The residue is dissolved in ethyl acetate, and the solution is washed with water, dried and then concentrated under reduced pressure to remove solvent. The residue is recrystallized from ether. 15.54 g of 2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine are obtained.

Workup

  1. concentrationthe mixture is concentrated under reduced pressure
  2. customto remove solvent
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washthe solution is washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto remove solvent
  8. customThe residue is recrystallized from ether

Sources & evidence

ORD record
ord-46245ad98a7644dbbba7e7b2ed233ffd
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

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