Benzoic acid, 2-isothiocyanato-, methyl ester → 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]propyl]-2,3-dihydro-2-thioxo-4(1H)-quinazolinone

HRID 1248248Notes

Reaction equation

HRID 1248248 reaction equation
[N:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=O)=[C:2]=[S:3].[NH2:14][CH2:15][CH:16]([N:18]1[CH2:23][CH2:22][CH:21]([C:24]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[O:25])[CH2:20][CH2:19]1)[CH3:17]>O1CCCC1>[F:32][C:29]1[CH:28]=[CH:27][C:26]([C:24]([CH:21]2[CH2:20][CH2:19][N:18]([CH:16]([CH3:17])[CH2:15][N:14]3[C:6](=[O:8])[C:5]4[C:4](=[CH:13][CH:12]=[CH:11][CH:10]=4)[NH:1][C:2]3=[S:3])[CH2:23][CH2:22]2)=[O:25])=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 85243Benzoic acid, 2-isothiocyanato-, methyl esterHCID 20278960HCID 20278960, compound

Product 1

HCID 128520723-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]propyl]-2,3-dihydro-2-thioxo-4(1H)-quinazolinoneYield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6.7 parts of methyl 2-isothiocyanatobenzoate, 8 parts of [1-(2-amino-1-methylethyl)-4-piperidinyl](4-fluorophenyl)methanone and 108 parts of tetrahydrofuran is stirred overnight at room temperature. The reaction mixture is evaporated. The residue is purified twice by column-chromatography over silica gel using first a mixture of trichloromethane and methanol (90:10 by volume) and then a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized twice from 2-propanol, yielding 1.6 parts (13%) of 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]propyl]-2,3-dihydro-2-thioxo-4(1H)-quinazolinone; mp. 160.6° C.

Workup

  1. customThe reaction mixture is evaporated
  2. customThe residue is purified twice by column-chromatography over silica gel using first
  3. additiona mixture of trichloromethane and methanol (90:10 by volume)
  4. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  5. customThe pure fractions are collected
  6. customthe eluent is evaporated
  7. customThe residue is crystallized twice from 2-propanol

Sources & evidence

ORD record
ord-f9d7e0638bf84af18f851baa8f614e47
Source dataset
uspto-grants-1985_06
Patent number
US04522945

Reaction notes

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