Malic Acid → Varenicline Malate

HRID 2092910

Reaction equation

HRID 2092910 reaction equation
[CH:1]1[CH:2]=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][C:7]1[CH:11]3[CH2:16][NH:15][CH2:14][CH:13]([C:6]=1[CH:5]=2)[CH2:12]3.[C:17]([OH:25])(=[O:24])[CH:18]([CH2:20][C:21]([OH:23])=[O:22])[OH:19]>CC(O)C>[CH:2]1[CH:1]=[N:10][C:9]2[C:4]([N:3]=1)=[CH:5][C:6]1[CH:13]3[CH2:14][NH:15][CH2:16][CH:11]([C:7]=1[CH:8]=2)[CH2:12]3.[C:17]([O-:25])(=[O:24])[CH:18]([CH2:20][C:21]([O-:23])=[O:22])[OH:19]

Participants

4

Reactant 2

HCID 525Malic AcidHCID 1703615,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaene

Product 1

HCID 86653157Varenicline Malate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of Varenicline base (1 g) in 2-propanol (15 mL) at 40° C., malic acid (1.55 g) was added. The resulting suspension was heated at 40° C. for 1 h and allowed to cool to ambient temperature for 5 h. Finally, the solid was filtered and dried at 40° C. under vacuum. HPLC purity: 99.70%; XRD Analysis: Form III.

Workup

  1. temperatureto cool to ambient temperature for 5 h
  2. filtrationFinally, the solid was filtered
  3. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-67b8cddde33346588060f63ce2bb82e7
Source dataset
uspto-grants-2013_05
Patent number
US08440825B2

Linked notes

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