Tetrafluoro-m-phenylenediamine dihydrochloride → 3-Amino-4-[(3-{3-[(piperidin-1-yl)methyl]phenoxy}propyl)amino]-1H-1lambda~4~,2,5-thiadiazol-1-one

HRID 1980732Notes

Reaction equation

HRID 1980732 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(N)C(F)=C(F)C(F)=C([NH2:28])C=1F.Cl.Cl.CO[C:35]1[C:39](OC)=[N:38][S:37](=[O:42])[N:36]=1>CO>[NH2:28][C:35]1[C:39]([NH:15][CH2:14][CH2:13][CH2:12][O:11][C:10]2[CH:16]=[CH:17][CH:18]=[C:8]([CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:9]=2)=[N:38][S:37](=[O:42])[N:36]=1

Participants

5

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineHCID 129139473,4-Dimethoxy-1,2,5-thiadiazole 1-oxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 3-(3-piperidinomethylphenoxy)propylamine (from the dihydrochloride, 4.0 g; 12.4 mmoles) in 40 ml of methanol was added dropwise over a period of 50 minutes to a solution of 3,4-dimethoxy-1,2,5-thiadiazole 1-oxide (2.01 g; 12.4 mmoles) in 200 ml of methanol that had been cooled to 0° in an ice-water bath. After 15 minutes, anhydrous ammonia was bubbled into the solution for 5 minutes and the solution then was stirred at ambient temperature for 17 hours. The reaction mixture was evaporated under reduced pressure and the residue chromatographed by flash chromatography on 100 g of silica gel (230-400 mesh) using methanol-acetonitrile. The appropriate fractions were combined and evaporated to give 4.18 g of product. Recrystallization from 95% aqueous ethanol yielded the title compound, mp 155°-157° (dec.).

Workup

  1. temperaturehad been cooled to 0° in an ice-water bath
  2. customanhydrous ammonia was bubbled into the solution for 5 minutes
  3. customThe reaction mixture was evaporated under reduced pressure
  4. customthe residue chromatographed by flash chromatography on 100 g of silica gel (230-400 mesh)
  5. customevaporated

Sources & evidence

ORD record
ord-0b77d44673f84a468d5d6d75cfa0270d
Source dataset
uspto-grants-1985_04
Patent number
US04510309

Reaction notes

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