Potassium Iodide → 1'-[2-(6-benzothiazolyl)ethyl]-3,4-dihydro-6-methanesulfonamidospiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one hydrochloride

HRID 1591196Notes

Reaction equation

HRID 1591196 reaction equation
[ClH:1].[CH3:2][S:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]2[O:20][C:14]3([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH2:13][C:12](=[O:21])[C:11]=2[CH:22]=1)(=[O:5])=[O:4].C(=O)(O)[O-].[Na+].CS(O[CH2:33][CH2:34][C:35]1[CH:43]=[CH:42][C:38]2[N:39]=[CH:40][S:41][C:37]=2[CH:36]=1)(=O)=O.[I-].[K+]>C(#N)C>[ClH:1].[S:41]1[C:37]2[CH:36]=[C:35]([CH2:34][CH2:33][N:17]3[CH2:16][CH2:15][C:14]4([CH2:13][C:12](=[O:21])[C:11]5[CH:22]=[C:7]([NH:6][S:3]([CH3:2])(=[O:4])=[O:5])[CH:8]=[CH:9][C:10]=5[O:20]4)[CH2:19][CH2:18]3)[CH:43]=[CH:42][C:38]=2[N:39]=[CH:40]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 19045253N-(4-Oxospiro[chroman-2,4'-piperidine]-6-yl)methanesulfonamide hydrochlorideHCID 54001247HCID 54001247, compound

Product 1

HCID 190455751'-[2-(6-benzothiazolyl)ethyl]-3,4-dihydro-6-methanesulfonamidospiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one hydrochlorideYield 48%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a manner similar to that described in Example 92, Step B a mixture of 3,4-dihydro-6-methanesulfonamido-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one hydrochloride (0.146 g, 0.42 mmol), sodium bicarbonate (0.143 g, 1.70 mmol), 6-benzothiazolylethyl methanesulfonate (0.108 g, 0.42 mmol), potassium iodide (0.070 g, 0.42 mmol) and acetonitrile (5 mL) was heated at reflux for 6.5 hours. Purification and crystallization as the hydrochloride salt from ethanol gave 0.102 g (48%) of the title compound as a white solid, mp 214°-215° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6.5 hours
  3. customPurification and crystallization as the hydrochloride salt from ethanol

Sources & evidence

ORD record
ord-5156ce76f65240f9816fcef26276eca7
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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