Piperidine → Minoxidil

HRID 1087876

Reaction equation

HRID 1087876 reaction equation
C([O:4][N:5]1[C:10]([NH2:11])=[CH:9][C:8](Cl)=[N:7][C:6]1=[NH:13])(=O)C.[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[OH-].[Na+]>C(O)C>[NH2:11][C:10]1[N:5]([OH:4])[C:6](=[NH:13])[N:7]=[C:8]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:9]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 14798Sodium HydroxideHCID 221641673-(Acetyloxy)-6-chloro-2-imino-2,3-dihydropyrimidin-4-amine

Product 1

HCID 4201Minoxidil

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.01 g (5 mmoles) of 1-acetoxy-6-amino-4-chloro-1,2-dihydro-2-iminopyrimidine are added under stirring to a mixture containing 10 ml of ethanol and 3 ml of piperidine. The mixture is refluxed while stirring for 30 minutes, then 5 ml of 1N aqueous sodium hydroxide solution are added and the boiling is continued for additional 30 minutes. Thereafter, the mixture is evaporated under reduced pressure and the residue is mixed with 10 ml of water. The crystalline precipitate is filtered, washed with water and dried to give the aimed compound in a yield of 0.85 g (82%), m.p.: 262°-266° C.

Workup

  1. temperatureThe mixture is refluxed
  2. stirringwhile stirring for 30 minutes
  3. customThereafter, the mixture is evaporated under reduced pressure
  4. additionthe residue is mixed with 10 ml of water
  5. filtrationThe crystalline precipitate is filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-8a67e9b6af534d27bbc65652335ee57c
Source dataset
uspto-grants-1990_10
Patent number
US04960888

Linked notes

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