Benzoic Acid → Rizatriptan Benzoate

HRID 1180101

Reaction equation

HRID 1180101 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][N:11]([CH2:13][CH2:14][C:15]1[C:19]2[CH:20]=[C:21]([CH2:24][N:25]3[N:29]=[CH:28][N:27]=[CH:26]3)[CH:22]=[CH:23][C:18]=2[NH:17][CH:16]=1)[CH3:12]>C(OC(C)C)(=O)C.C(O)(C)C>[CH3:10][N:11]([CH2:13][CH2:14][C:15]1[C:19]2[CH:20]=[C:21]([CH2:24][N:25]3[N:29]=[CH:28][N:27]=[CH:26]3)[CH:22]=[CH:23][C:18]=2[NH:17][CH:16]=1)[CH3:12].[CH:5]1[CH:4]=[CH:3][C:2]([C:1]([OH:9])=[O:8])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 243Benzoic AcidHCID 5078Rizatriptan

Product 1

HCID 77997Rizatriptan BenzoateYield 80.1%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 7915Isopropyl AcetateSolvent

Procedure

A solution of 147 mg (1.2 mmoles) of benzoic acid in 1 ml of isopropyl acetate was added slowly to a solution of 300 mg (1.1 mmoles) of the rizatriptan base in 2.6 ml of isopropyl alcohol. The mixture was stirred at room temperature for 30 minutes and evaporated to dryness, and the residue recrystallised from ethanol to give 345 mg (80%) of rizatriptan benzoate as a white crystalline solid.

Workup

  1. customevaporated to dryness
  2. customthe residue recrystallised from ethanol

Sources & evidence

ORD record
ord-abd210887dcd46259279e7ded4ab972d
Source dataset
uspto-grants-2007_10
Patent number
US07279581B2

Linked notes

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