Water → Azafenidin

HRID 341963Notes

Reaction equation

HRID 341963 reaction equation
Cl[C:2]([N:4]1[CH2:9][CH2:8][CH2:7][CH:6]=[C:5]1Cl)=[O:3].[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([O:19][CH2:20][C:21]#[CH:22])=[CH:14][C:13]=1[NH:23][NH:24]C=O.C(N(CC)CC)C.O>C(#N)C>[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([O:19][CH2:20][C:21]#[CH:22])=[CH:14][C:13]=1[N:23]1[C:2](=[O:3])[N:4]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]2=[N:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10866933HCID 10866933, compoundHCID 10999770HCID 10999770, compound

Product 1

HCID 443029Azafenidin

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

N-Chlorocarbonyl-2-chloro-1,4,5,6-tetrahydro-pyridine (4.32 g, 0.024 mol) dissolved in 20 ml acetonitrile are added to a stirred suspension of formic acid N'-(2,4-dichloro-5-(2-propinyloxy)-phenyl) hydrazide (5.18 g, 0.02 mol) in 250 ml acetonitrile at 0°-10° C. for 20 minutes. This is then reacted at the same temperature with triethylamine (4.04 g, 0.04 mol) and dissolved in 20 ml acetonitrile. This is stirred for one hour at 5°-10° C. and a colourless precipitate precipitates out. This is heated for 4 hours to 50°-55° C. and then stirred for one night at room temperature. The batch is reacted with 30 ml 6N hydrochloric acid and stirred for 1 hour at 50° C. The solvent is drawn off under reduced pressure and the residue digested with iced water. The resultant pale grey precipitate is separated by filtration, washed with water and dried at 50°-60° C. Yield: 6.6 g (=97.6%) Melting point: 160°-162° C.

Workup

  1. customa colourless precipitate precipitates out
  2. temperatureThis is heated for 4 hours to 50°-55° C.
  3. stirringstirred for one night at room temperature
  4. customThe batch is reacted with 30 ml 6N hydrochloric acid
  5. stirringstirred for 1 hour at 50° C
  6. customThe resultant pale grey precipitate is separated by filtration
  7. washwashed with water
  8. customdried at 50°-60° C

Sources & evidence

ORD record
ord-5bb9fd3fb4ac44038baad78f8484f636
Source dataset
uspto-grants-1999_01
Patent number
US05856495

Reaction notes

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