2,3-Dihydroxybutanedioic Acid → Champix

HRID 1879292

Reaction equation

HRID 1879292 reaction equation
[N:1]1[C:16]2[C:5](=[CH:6][C:7]3[CH:13]4[CH2:14][CH:9]([CH2:10][NH:11][CH2:12]4)[C:8]=3[CH:15]=2)[N:4]=[CH:3][CH:2]=1.[C:17]([OH:26])(=[O:25])[CH:18]([CH:20]([C:22]([OH:24])=[O:23])[OH:21])[OH:19]>CO>[CH:2]1[CH:3]=[N:4][C:5]2[C:16]([N:1]=1)=[CH:15][C:8]1[CH:9]3[CH2:10][NH:11][CH2:12][CH:13]([C:7]=1[CH:6]=2)[CH2:14]3.[CH:18]([OH:19])([C:17]([OH:26])=[O:25])[CH:20]([OH:21])[C:22]([OH:24])=[O:23]

Participants

4

Reactant 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 1703615,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaene

Product 1

HCID 46783232ChampixYield 99.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
22.5 °C

Procedure

7,8,9,10-Tetrahydro-6,10-methano-6H-pyrazino-[2,3-h][3]benzazepine (50 g) was dissolved in methanol (375 ml) and the solution was added to a solution of tartaric acid (39.31 g) dissolved in methanol (375 ml) at 20-25° C. The suspension was stirred for 1 hour 30 minutes at 20-25° C. followed by filtration of the solid and then drying to yield 82 g of varenicline tartrate (Purity by HPLC: 99.9%).

Workup

  1. filtrationfollowed by filtration of the solid
  2. customdrying

Sources & evidence

ORD record
ord-4b9bbe76b2124621bd49fff88507b42a
Source dataset
uspto-grants-2012_11
Patent number
US08314235B2

Linked notes

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