Oxalic Acid → 4-Chloro-2-[[(1R)-4-(methylamino)-1-phenylbutyl]oxy]benzonitrile ethanedioate

HRID 352105Notes

Reaction equation

HRID 352105 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C@@H:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13][CH2:14]I)[CH:3]=1.[C:22]([OH:27])(=[O:26])[C:23]([OH:25])=[O:24].[CH3:28][NH2:29]>O1CCCC1.CO>[C:22]([OH:27])(=[O:26])[C:23]([OH:25])=[O:24].[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C@@H:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13][CH2:14][NH:29][CH3:28])[CH:3]=1

Participants

6

Reactant 3

HCID 971Oxalic AcidHCID 6329MethylamineHCID 698282664-Chloro-2-[[(1r)-4-iodo-1-phenylbutyl]oxy]benzonitrile

Product 1

HCID 865883464-Chloro-2-[[(1R)-4-(methylamino)-1-phenylbutyl]oxy]benzonitrile ethanedioate

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from step (c) (286 mg) in 40% aqueous methylamine (1 ml) and tetrahydrofuran (10 ml) was stirred for 6 h. The solvent was removed in vacuo and the residue dissolved in water and extracted with ethyl acetate (three times). The combined organic extracts were washed with water, dried (magnesium sulphate) and evaporated to give an oil. To a solution of this amine in methanol (10 ml) was added a solution of oxalic acid (57 mg) in methanol. The solvent was removed in vacuo and the residue triturated with ethyl acetate. The solid was collected and dried to afford the title compound as a white solid (110 mg). M.p. 167-169° C.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in water
  3. extractionextracted with ethyl acetate (three times)
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried (magnesium sulphate)
  6. customevaporated
  7. customto give an oil
  8. customThe solvent was removed in vacuo
  9. customthe residue triturated with ethyl acetate
  10. customThe solid was collected
  11. customdried

Sources & evidence

ORD record
ord-a8efe481e17d42438c85c8a6137a7583
Source dataset
uspto-grants-2004_06
Patent number
US06743939B2

Reaction notes

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