Piperidine → Minoxidil

HRID 1087879

Reaction equation

HRID 1087879 reaction equation
C([NH:4][C:5]1[N:10]([O:11]C(=O)C)[C:9](=[NH:15])[N:8]=[C:7](Cl)[CH:6]=1)(=O)C.[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>C(Cl)(Cl)Cl>[NH2:4][C:5]1[N:10]([OH:11])[C:9](=[NH:15])[N:8]=[C:7]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:6]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 140351387HCID 140351387, compound

Product 1

HCID 4201MinoxidilYield 80%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

After adding 0.49 g (2 mmoles) of 6-acetamido-1-acetoxy-4-chloro-1,2-dihydro-2-iminopyrimidine to a solution containing 10 ml of chloroform and 2 ml of piperidine, the mixture is refluxed for 30 minutes, then evaporated under reduced pressure. The residue is dissolved in the mixture of 10 ml of ethanol and 3 ml of 1N aqueous sodium hydroxide solution. The reaction mixture is left to stand at room temperature for one hour and then again evaporated under reduced pressure. After taking up the residue in 10 ml of water, the crystals are filtered, washed with water and dried to give 0.34 g (80% yield) of the aimed compound which shows no melting point depression when mixed with the product of Example 1.

Workup

  1. temperaturethe mixture is refluxed for 30 minutes
  2. customevaporated under reduced pressure
  3. dissolutionThe residue is dissolved in the mixture of 10 ml of ethanol and 3 ml of 1N aqueous sodium hydroxide solution
  4. waitThe reaction mixture is left
  5. customagain evaporated under reduced pressure
  6. filtrationthe crystals are filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-eb2884709fd640a4a9e2fb4a93e1f856
Source dataset
uspto-grants-1990_10
Patent number
US04960888

Linked notes

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