HCID 10669852, compound → HCID 10717063, compound

HRID 1460119Notes

Reaction equation

HRID 1460119 reaction equation
[CH2:1]([N:4]1[C@H:9]([CH3:10])[CH2:8][N:7]([C@@H:11]([C:19]2[S:20][CH:21]=[C:22]([Br:24])[CH:23]=2)[C:12]2[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=2)[C@@H:6]([CH3:25])[CH2:5]1)[CH:2]=[CH2:3]>C(O)C>[CH2:1]([N:4]1[C@@H:9]([CH3:10])[CH2:8][N:7]([C@H:11]([C:19]2[S:20][CH:21]=[C:22]([Br:24])[CH:23]=2)[C:12]2[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=2)[C@H:6]([CH3:25])[CH2:5]1)[CH:2]=[CH2:3]

Participants

3

Reactant 1

HCID 10669852HCID 10669852, compound

Product 1

HCID 10717063HCID 10717063, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 4.22 g (11 mmol) of (-)-p-ditoluoyl-L-tartaric acid in 15 mL of absolute ethanol was added to a suspension of 2.3 g (5.5 mmol) of (±)-3-((R*)-((2S*,5R*)-4-allyl-2,5-dimethyl-1-piperazinyl)(4-bromo-2-thienyl)methyl)phenol (Example 42) in 5 mL of absolute ethanol. The mixture was heated to boiling and the resulting clear solution was allowed to crystallize at room temperature. After three crystallizations, the salt was converted to the free amine as in Example 65 and recrystallized from absolute ethanol to give 0.490 g (43% of theoretical for one enantiomer) of (±)-3-((S)-((2R,5S)-4-allyl-2,5-dimethyl-1-piperazinyl)(4-bromo-2-thienyl)methyl)phenol as white crystals, mp 183°-185° C. Absolute configuration was determined by x-ray crystallography. [α]D20 =+14.50° (tetrahydrofuran, c=3.3). HPLC on β-cyclodextrin with methanol:0.1M ammonium acetate/1:1 gave one peak at tR =11 min. Calc. for C20H25BrN2OS: C, 57.00; H, 5.98; N, 6.65; Br, 18.96; S, 7.61. Found: C, 56.93; H, 5.99; N, 6.67; Br, 19.04; S, 7.67.

Workup

  1. temperatureThe mixture was heated
  2. customto crystallize at room temperature
  3. customAfter three crystallizations
  4. customrecrystallized from absolute ethanol

Sources & evidence

ORD record
ord-b660c88be04f4832910fa37b2550c9e9
Source dataset
uspto-grants-1998_12
Patent number
US05854249

Reaction notes

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