Methanol → HCID 13519406, compound

HRID 370710Notes

Reaction equation

HRID 370710 reaction equation
[C:1]([N:3]1[CH2:8][CH2:7][CH:6]([C:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[S:11][N:10]=2)[CH2:5][CH2:4]1)#[N:2].[C-]#N.[K+].[CH3:21][OH:22]>>[CH3:21][O:22][C:1]([N:3]1[CH2:8][CH2:7][CH:6]([C:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[S:11][N:10]=2)[CH2:5][CH2:4]1)=[NH:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 9032Potassium CyanideHCID 13324092HCID 13324092, compound

Product 1

HCID 13519406HCID 13519406, compound

Procedure

A mixture of 3-(1-cyano-4-piperidinyl)-1,2-benzisothiazole (11.7 g, 0.048 mole), KCN (3.1 g) and MeOH (145 ml) was stirred and refluxed for 4 hours, and then stirred at ambient temperature for 14 hours. The MeOH was removed in vacuo and the residue diluted with water. The aqueous suspension was extracted with chloroform and the chloroform extract was washed with water and dried over MgSO4. Thereafter, the chloroform was evaporated in vacuo to yield 12.4 g of a solid. Recrystallization from EtOAc yielded 6.0 g (45.2%) of a solid. An analytical sample was obtained by a second recrystallization of a 3.5 g sample. The resultant solid (2.6 g) had a melting point of 144°-146° C.

Workup

  1. temperaturerefluxed for 4 hours
  2. stirringstirred at ambient temperature for 14 hours
  3. customThe MeOH was removed in vacuo
  4. additionthe residue diluted with water
  5. extractionThe aqueous suspension was extracted with chloroform
  6. extractionthe chloroform extract
  7. washwas washed with water
  8. dry with materialdried over MgSO4
  9. customThereafter, the chloroform was evaporated in vacuo

Sources & evidence

ORD record
ord-e550610efe8b4b86b13defcf41b242f6
Source dataset
uspto-grants-1985_07
Patent number
US04528292

Reaction notes

Loading…