Hydrochloric Acid → HCID 178478600, compound

HRID 745865Notes

Reaction equation

HRID 745865 reaction equation
[NH2:1][C:2]1[C:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:13]=2)=[N:5]S(=O)[N:3]=1.[ClH:26]>CO.C(O)C>[ClH:26].[ClH:26].[ClH:26].[N:19]1([CH2:18][C:14]2[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=2)[O:11][CH2:10][CH2:9][CH2:8][NH:7][C:6](=[NH:5])[C:2](=[NH:1])[NH2:3])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54868833-Amino-4-[(3-{3-[(piperidin-1-yl)methyl]phenoxy}propyl)amino]-1H-1lambda~4~,2,5-thiadiazol-1-one

Product 1

HCID 178478600HCID 178478600, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A suspension of 3-amino-4-[3-(3-piperidinomethylphenoxy)propylamino]-1,2,5-thiadiazole 1-oxide (17.1 g; 47.0 mmoles) [prepared according to published United Kingdom Patent Application No. 2,067,987] in 450 mL of methanol was treated with 38 mL of concentrated HCl. The resultant solution was stirred for 3 hours at ambient temperature. Concentration of the solution followed by azeotropic removal of water with absolute ethanol gave colorless crystals. These were suspended in 200 mL of absolute ethanol, filtered and dried under vacuum to give 16.6 g (82.6%) of the title compound, m.p. 205°-222° C. (dec.). Recrystallization from 50% methanolethyl acetate gave an analytical sample, m.p. 206°-216° C. (dec.).

Workup

  1. customConcentration of the solution followed by azeotropic removal of water with absolute ethanol
  2. customgave colorless crystals
  3. filtrationfiltered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f7c2ff35e1124d93a80cae0feb9f6375
Source dataset
uspto-grants-1986_07
Patent number
US04600779

Reaction notes

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