Ammonia → 1-[3-{4-(diphenylmethyl)piperazin-1-yl}propyl]4-amino-2(1H)-quinazolinone

HRID 365101Notes

Reaction equation

HRID 365101 reaction equation
[C:1]1([CH:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20](=S)[NH:19][C:18]3=[O:28])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH3:35]>C(Cl)(Cl)Cl.CO>[C:1]1([CH:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]([NH2:35])=[N:19][C:18]3=[O:28])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 140145691-[3-{4-(diphenylmethyl)piperazin-1-yl}propyl]-4-thioxo-3,4-dihydro-2(1H)-quinazolinone

Product 1

HCID 134883801-[3-{4-(diphenylmethyl)piperazin-1-yl}propyl]4-amino-2(1H)-quinazolinone

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

A solution of 1-[3-{4-(diphenylmethyl)piperazin-1-yl}propyl]-4-thioxo-3,4-dihydro-2(1H)-quinazolinone (1.2 g) in chloroform (25 ml) and 20% ammonia in methanol (30 ml) was heated in an autoclave for 15 hours at 100° C. The reaction mixture was concentrated in vacuo and the residue was purified by subjecting to a column chromatography on silica gel using 5% methanol in chloroform for elution to give an oily residue. This oily residue was dissolved in methanol and this solution was acidified with conc.hydrochloric acid solution and then concentrated in vacuo to give a crystal of the object compound, which was recrystallized twice from a mixture of water and isoporpyl alcohol to give 1-[3-{4-(diphenylmethyl)piperazin-1-yl}propyl]-4-amino-2(1H)-quinazolinone.2HCl.H2O (0.6 g).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified
  3. washby subjecting to a column chromatography on silica gel using 5% methanol in chloroform for elution
  4. customto give an oily residue
  5. concentrationhydrochloric acid solution and then concentrated in vacuo
  6. customto give a crystal of the object compound, which
  7. customwas recrystallized twice from a mixture of water and isoporpyl alcohol

Sources & evidence

ORD record
ord-d2af8eb63f5d4c74a91d904c31b56b03
Source dataset
uspto-grants-1986_08
Patent number
US04608375

Reaction notes

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