Potassium Iodide → HCID 67925653, compound

HRID 1085690Notes

Reaction equation

HRID 1085690 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH3:7][O:8][C@H:9]1[C@@H:14]([N:15]([CH3:25])[C:16]2[S:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)[CH2:13][CH2:12][NH:11][CH2:10]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH2:43][CH2:44][CH2:45]Cl)=[CH:37][CH:36]=1>O.CC(C)CC(=O)C>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH2:43][CH2:44][CH2:45][N:11]2[CH2:12][CH2:13][C@H:14]([N:15]([CH3:25])[C:16]3[S:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)[C@H:9]([O:8][CH3:7])[CH2:10]2)=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 12928632HCID 12928632, compoundHCID 67925671HCID 67925671, compound

Product 1

HCID 67925653HCID 67925653, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5.5 parts of cis-N-(3-methoxy-4-piperidinyl)-N-methyl-2-benzothiazolamine ethanedioate(1:1), 10.6 parts of sodium carbonate, 0.1 parts of potassium iodide and 200 parts of 4-methyl-2-pentanone was stirred and refluxed for 30 minutes. After cooling to 60° C., 4.4 parts of 1-chloro-4-(4-chlorobutoxy)benzene were added. The whole was stirred and refluxed overnight. After cooling, water was added and the layers were separated. The organic layer was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the ethanedioate salt in 2-propanol. The salt was filtered off and dried, yielding 6 parts (73%) of cis-N-[1-[4-(4-chlorophenoxy)-butyl]-3-methoxy-4-piperidinyl]-N-methyl-2-benzothiazolamine ethanedioate(1:1); mp. 210.4° C. (205).

Workup

  1. temperaturerefluxed for 30 minutes
  2. stirringThe whole was stirred
  3. temperaturerefluxed overnight
  4. temperatureAfter cooling
  5. customthe layers were separated
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated
  13. filtrationThe salt was filtered off
  14. customdried

Sources & evidence

ORD record
ord-e772d0cb2209438faa3fbc1995775c37
Source dataset
uspto-grants-1991_04
Patent number
US05010198

Reaction notes

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