HCID 10688691, compound → HCID 22875657, compound

HRID 2258351Notes

Reaction equation

HRID 2258351 reaction equation
[CH2:1]([N:4]1[C@H:9]([CH3:10])[CH2:8][N:7]([C@@H:11]([C:19]2[CH:23]=[CH:22][S:21][CH:20]=2)[C:12]2[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=2)[C@@H:6]([CH3:24])[CH2:5]1)[CH:2]=[CH2:3].C1(C)C=CC(C([C@@](C(O)=O)(O)[C@@](C(C2C=CC(C)=CC=2)=O)(O)C(O)=O)=O)=CC=1>C(O)C>[CH2:1]([N:4]1[C@@H:9]([CH3:10])[CH2:8][N:7]([C@H:11]([C:19]2[CH:23]=[CH:22][S:21][CH:20]=2)[C:12]2[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=2)[C@H:6]([CH3:24])[CH2:5]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 10688691HCID 10688691, compoundHCID 29414711Di-para-toluoyl-L-tartaric acid

Product 1

HCID 22875657HCID 22875657, compoundYield 7.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(±)-3-((R*)-((2S*,5R*)-4-Allyl-2,5-dimethyl-1-piperazinyl)(3-thienyl)methyl)phenol (2.74 g, 8.0 mmol, Example 63) was added to a solution of 6.18 g (16 mmol) of (-)-di-p-toluoyl-L-tartaric acid in 20 mL of absolute ethanol. The mixture was warmed to complete solution, cooled and allowed to crystallize at room temperature. After four recrystallizations, the salt was dissolved in 20 mL of 1N aqueous sodium hydroxide, and the solution was titrated to pH 8 with 6N hydrochloric acid. The precipitated amine was collected by filtration and recrystallized from absolute ethanol to give 0.21 g of (-)-3-((S)-((2R,5S)-4-allyl-2,5-dimethyl-1-piperazinyl)(3-thienyl)methyl)phenol as white crystals, mp 193°-194° C. [α]D20 =-3.2° (ethyl acetate, c=1.4). HPLC on β-cyclodextrin with methanoh0.1M ammonium acetate/1:1 gave one peak at tR =7.8 min. Calc. for C20H26N2OS: C, 70.14; H, 7.65: N, 8.18: S, 9.36. Found: C, 70.24; H, 7.69; N, 8.23; S, 9.42.

Workup

  1. temperatureThe mixture was warmed to complete solution
  2. temperaturecooled
  3. customto crystallize at room temperature
  4. customAfter four recrystallizations
  5. dissolutionthe salt was dissolved in 20 mL of 1N aqueous sodium hydroxide
  6. filtrationThe precipitated amine was collected by filtration
  7. customrecrystallized from absolute ethanol

Sources & evidence

ORD record
ord-fd64017d41714e58ac5835164a91dd70
Source dataset
uspto-grants-1997_08
Patent number
US05658908

Reaction notes

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