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Cysteamine → 2-{2-[2-(4-(3-Fluorophenyl)-1,2,3,6-tetrahydropyridin-1-yl)ethyloxy]phenyl}thiazolidine

HRID 867910
Notes
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Reaction equation

HRID 867910 reaction equation
[NH2:1][CH2:2][CH2:3][SH:4].[OH-].[Na+].[F:7][C:8]1[CH:9]=[C:10]([C: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]=O)[CH2:18][CH:19]=2)[CH:11]=[CH:12][CH:13]=1>C(O)C>[F:7][C:8]1[CH:9]=[C:10]([C: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]3[NH:1][CH2:2][CH2:3][S:4]3)[CH2:16][CH:15]=2)[CH:11]=[CH:12][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6058CysteamineHCID 14798Sodium HydroxideHCID 138430162-{2-[4-(3-Fluorophenyl)-1,2,3,6-tetrahydropyridin-1-yl]ethyloxy}benzaldehyde

Product 1

HCID 137496142-{2-[2-(4-(3-Fluorophenyl)-1,2,3,6-tetrahydropyridin-1-yl)ethyloxy]phenyl}thiazolidineYield 86.9%

Reagents, catalysts & solvents 1

HCID 702Ethanol
Solvent
2×

Procedure

8.09 g of cysteamine hydrochlorideare dissolved in 450 ml of ethanol, and 2.93 g of sodium hydroxide are added thereto. The mixture is stirred at room temperature for 10 minutes. A solution of 21.05 g of 2-{2-[4-(3-fluorophenyl)-1,2,3,6-tetrahydropyridin-1-yl]ethyloxy}benzaldehyde in 50 ml of ethanol is added to the mixture, and the mixture is further stirred at room temperature for 14 hours. The mixture is concentrated and then extracted with ethyl acetate. The extract is washed with a saturated sodium chloride solution, dried and then evaporated to remove the solvent. The residue is recrystallized from n-hexane. 21.62 g of 2-{2-[2-(4-(3-fluorophenyl)-1,2,3,6-tetrahydropyridin-1-yl)ethyloxy]phenyl}thiazolidine are obtained. Yield: 69%.

Workup

  1. stirringthe mixture is further stirred at room temperature for 14 hours
  2. concentrationThe mixture is concentrated
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with a saturated sodium chloride solution
  5. customdried
  6. customevaporated
  7. customto remove the solvent
  8. customThe residue is recrystallized from n-hexane

Sources & evidence

ORD record
ord-09a2bf1ceca247489670ab60b4ccb608
Source dataset
uspto-grants-1988_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04777178

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes