O-(1,1-Dimethylethyl) S-(4,6-dimethyl-2-pyrimidinyl) carbonothioate → 1-[3-(4-t-Butoxycarbonylamino-2-methoxyphenoxy)-n-propyl]-4-phenyl-piperazine

HRID 1648783Notes

Reaction equation

HRID 1648783 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[C:4]([O:24][CH3:25])[CH:3]=1.[C:26]([O:30][C:31](SC1N=C(C)C=C(C)N=1)=[O:32])([CH3:29])([CH3:28])[CH3:27]>O1CCCC1>[C:26]([O:30][C:31]([NH:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:14][CH2:15]2)=[C:4]([O:24][CH3:25])[CH:3]=1)=[O:32])([CH3:29])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 148428O-(1,1-Dimethylethyl) S-(4,6-dimethyl-2-pyrimidinyl) carbonothioateHCID 12838104HCID 12838104, compound

Product 1

HCID 128381111-[3-(4-t-Butoxycarbonylamino-2-methoxyphenoxy)-n-propyl]-4-phenyl-piperazineYield 101.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1 g of 1-[3-(4-amino-2-methoxyphenoxy)-n-propyl]-4-phenyl-piperazine, 1.06 g of 2-(t-butoxycarbonylthio)-4,6-dimethylpyrimidine and 15 ml of anhydrous tetrahydrofuran is refluxed for 65 hours. After the reaction, the mixture is evaporated under reduced pressure to remove tetrahydrofuran. Methylene chloride is added to the residue, and the mixture is washed with an aqueous 10% sodium hydroxide solution and water, successively. Said mixture is dried and then evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel chromatography (Solvent; 1.5% methanol/chloroform), and then recrystallized from a mixture of benzene and n-hexane. 1.31 g of 1-[3-(4-t-butoxycarbonylamino-2-methoxyphenoxy)-n-propyl]-4-phenyl-piperazine are thereby obtained as colorless needles. Yield: 85%

Workup

  1. temperatureis refluxed for 65 hours
  2. customAfter the reaction
  3. customthe mixture is evaporated under reduced pressure
  4. customto remove tetrahydrofuran
  5. additionMethylene chloride is added to the residue
  6. washthe mixture is washed with an aqueous 10% sodium hydroxide solution and water
  7. customis dried
  8. customevaporated under reduced pressure
  9. customto remove the solvent
  10. customThe residue is purified by silica gel chromatography (Solvent; 1.5% methanol/chloroform)
  11. customrecrystallized from a mixture of benzene and n-hexane

Sources & evidence

ORD record
ord-bd1fd117cea24963b3807a818ac5736d
Source dataset
uspto-grants-1983_11
Patent number
US04413006

Reaction notes

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