Hydrochloride methanol → 4-fluoro-N-[4-methoxy-7-piperidine-4-yl-benzothiazol-2-yl]-benzamide hydrochloride

HRID 1582124Notes

Reaction equation

HRID 1582124 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[S:21][C:20]([NH:23][C:24](=[O:32])[C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)=[N:19][C:18]=3[C:17]([O:33][CH3:34])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:35].CO>>[ClH:35].[F:31][C:28]1[CH:27]=[CH:26][C:25]([C:24]([NH:23][C:20]2[S:21][C:22]3[C:14]([CH:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)=[CH:15][CH:16]=[C:17]([O:33][CH3:34])[C:18]=3[N:19]=2)=[O:32])=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 865888374-[2-(4-Fluoro-benzoylamino)-4-methoxy-benzothiazol-7-yl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 227195404-fluoro-N-[4-methoxy-7-piperidine-4-yl-benzothiazol-2-yl]-benzamide hydrochlorideYield 70%

Procedure

0.90 g (0.185 mMol) 4-[2-(4-fluoro-benzoylamino)-4-methoxy-benzothiazol-7-yl]-piperidine-1-carboxylic acid tert-butyl ester were dissolved in 3 ml 2.5 M HCl/MeOH and heated to reflux for 1.5 h. The reaction mixture was concentrated in vacuo and taken up in 4 ml isopropanol. The suspension formed was filtered and the material on the filter was washed with diethyl ether and dried in vacuo. One obtained 55 mg (70%) 4-fluoro-N-[4-methoxy-7-piperidine-4-yl-benzothiazol-2-yl]-benzamide hydrochloride (1:1) as a white solid. F.p.: 310-312° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1.5 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customThe suspension formed
  5. filtrationwas filtered
  6. washthe material on the filter was washed with diethyl ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-6082b7a7b3df4907bc6418df639676b5
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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