Atorvastatin → N-Benzylphenethylamine

HRID 1518932Notes

Reaction equation

HRID 1518932 reaction equation
CC(C1[N:8]([CH2:9][CH2:10][C@@H:11](O)[CH2:12][C@@H:13](O)[CH2:14][C:15](O)=O)[C:7](C2C=CC(F)=CC=2)=[C:6]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)C=1C(NC1C=CC=CC=1)=O)C>C(#N)C>[CH2:9]([NH:8][CH2:7][CH2:6][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

3

Reactant 1

HCID 60823Atorvastatin3×

Product 1

HCID 65055N-Benzylphenethylamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

The benethamine salt of atorvastatin (Form A) was synthesized by preparing a stock solution of the free acid of atorvastatin (U.S. Pat. No. 5,273,995) in acetonitrile (1 g in 40 mL of ACN). A solution of N-benzyl-2-phenylethylamine (benethamine) was prepared by dissolving 378.59 mg (1.0 equivalents) in acetonitrile (10 mL). The stock solution of atorvastatin free acid was added to the counterion solution with stirring. Over time, an additional 40 mL of acetonitrile was added to prevent the formation of a gel. After 5 days of stirring at ambient temperature, the solids were isolated by vacuum filtration using a Buchner funnel fitted with a paper filter (#2 Whatman). The solids were rinsed with acetonitrile (75 mL), and placed in a 25° C. oven under nitrogen to dry overnight to afford atorvastatin benethamine Form A.

Workup

  1. stirringAfter 5 days of stirring at ambient temperature
  2. customthe solids were isolated by vacuum filtration
  3. customfitted with a paper
  4. filtrationfilter (#2 Whatman)
  5. washThe solids were rinsed with acetonitrile (75 mL)
  6. customplaced in a 25° C.
  7. customto dry overnight

Sources & evidence

ORD record
ord-0aa98762d6a54b818c407c73dff1f9af
Source dataset
uspto-grants-2015_07
Patent number
US09073852B2

Reaction notes

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