Riluzole → HCID 14674474, compound

HRID 1085119Notes

Reaction equation

HRID 1085119 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.Cl.Cl[CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>CN(C)C=O>[NH:1]=[C:2]1[N:6]([CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[C:5]2[CH:7]=[CH:8][C:9]([O:11][C:12]([F:15])([F:13])[F:14])=[CH:10][C:4]=2[S:3]1

Participants

4

Reactant 2

HCID 5070RiluzoleHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochloride

Product 1

HCID 14674474HCID 14674474, compoundYield 20.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

2-Amino-6-trifluoromethoxybenzothiazole (9.4 g) and N-(2-chloroethyl)piperidine hydrochloride (8.1 g) are heated for 1 hour to 130° C. Dimethylformamide (20 cc) is then added and the reaction is continued for 24 hours at 130° C. After cooling of the mixture to a temperature in the region of 20° C., the precipitate is filtered off and then treated with 1N sodium hydroxide (50 cc) in distilled water (100 cc). The residue obtained by extraction with dichloromethane, drying over magnesium sulphate and concentration to dryness under reduced pressure (20 mm Hg; 2.7 kPa) is purified by chromatography on a silica column, with ethyl acetate and then a mixture of ethyl acetate and methanol (95:5 by volume) as eluents. 2-Imino-3-(2-piperidinoethyl)-6-trifluoromethoxybenzothiazoline (2.9 g) is obtained in the form of a yellow oil, which is converted to a dihydrochloride subliming at about 200° C. after recrystallization in boiling absolute ethanol (20 cc).

Workup

  1. filtrationthe precipitate is filtered off
  2. additiontreated with 1N sodium hydroxide (50 cc) in distilled water (100 cc)
  3. customThe residue obtained by extraction with dichloromethane
  4. dry with materialdrying over magnesium sulphate and concentration to dryness under reduced pressure (20 mm Hg; 2.7 kPa)
  5. customis purified by chromatography on a silica column, with ethyl acetate
  6. additiona mixture of ethyl acetate and methanol (95:5 by volume) as eluents

Sources & evidence

ORD record
ord-c1613f3f189849e2be3295239f4204fc
Source dataset
uspto-grants-1991_04
Patent number
US05008280

Reaction notes

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