Hydrochloride methanol → Morpholine-4-carboxylic acid (4-methoxy-7-piperidin-4-yl-benzothiazol-2-yl)-amide hydrochloride

HRID 1582147Notes

Reaction equation

HRID 1582147 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]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[O:25])=[N:19][C:18]=3[C:17]([O:32][CH3:33])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:34].CO>>[ClH:34].[CH3:33][O:32][C:17]1[C:18]2[N:19]=[C:20]([NH:23][C:24]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:25])[S:21][C:22]=2[C:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 865888464-{4-Methoxy-2-[(morpholine-4-carbonyl)-amino]-benzothiazol-7-yl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86588847Morpholine-4-carboxylic acid (4-methoxy-7-piperidin-4-yl-benzothiazol-2-yl)-amide hydrochlorideYield 67%

Procedure

0.45 g (0.094 mMol) 4-{4-Methoxy-2-[(morpholine-4-carbonyl)-amino]-benzothiazol-7-yl}-piperidine-1-carboxylic acid tert-butyl ester were dissolved in 2 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 5 ml isopropanol. The suspension formed was filtered and the material on the filter was washed with diethyl ether and dried in vacuo. One obtained 26 mg (67%) morpholine-4-carboxylic acid (4-methoxy-7-piperidin-4-yl-benzothiazol-2-yl)-amide hydrochloride (1:1) as a white solid. F.p.: 314-315° 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-b02dc449ce2746358b5dfea446ffd30e
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

Loading…