Hydrochloric Acid → Ethyl 3-[4-(6-Fluoro-1,2-benzisothiazol-3-yl)-1-piperidinyl]propionate hydrochloride

HRID 2184567Notes

Reaction equation

HRID 2184567 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[N:7][S:8][C:4]=2[CH:3]=1.[C:17]([O-:20])([O-])=[O:18].[K+].[K+].[CH3:23][C:24]#N.[ClH:26].[CH3:27][CH2:28]OCC>CCOC(C)=O.O>[ClH:26].[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:27][CH2:28][C:17]([O:20][CH2:23][CH3:24])=[O:18])[CH2:13][CH2:14]3)=[N:7][S:8][C:4]=2[CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 185049766-Fluoro-3-(4-piperidinyl)-1,2-benzisothiazole

Product 1

HCID 18467248Ethyl 3-[4-(6-Fluoro-1,2-benzisothiazol-3-yl)-1-piperidinyl]propionate hydrochlorideYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisothiazole (6.0 g, 25 mmol) ethyl 3-bromopropionate (4.5 g, 25 mmol), K2CO3 (3.5 g) and CH3CN (100 ml) was stirred and refluxed for 16 hours. The reaction was poured into H2O, and after extractive workup with EtOAc, 6.0 g of an orange oil was realized. The oil was dissolved in Et2O and ethereal HCl and added to precipitate 6.3 g of a white hydrochloride salt. The salt was recrystallized from CH3CN to yield 6.0 g (64% ) of the desired compound. An analytical sample was obtained by recrystallization of a 1.0 g sample from EtOH-Et2O to yield 0.8 g of a white solid, m.p.=197°-199° C. ANALYSIS: Calculated for C17H21FN2O2S.HCl: 54.76% C 5.95% H 7.51% N Found: 54.77% C 5.99% H 7.28% N

Workup

  1. temperaturerefluxed for 16 hours
  2. customto precipitate 6.3 g of a white hydrochloride salt
  3. customThe salt was recrystallized from CH3CN

Sources & evidence

ORD record
ord-bc9631e639d149d99488b3958728a8de
Source dataset
uspto-grants-2002_06
Patent number
USRE037729E1

Reaction notes

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