Potassium Iodide → 3-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-2-phenyl-4(3H)-quinazolinone

HRID 1248232Notes

Reaction equation

HRID 1248232 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[NH:21]1[CH2:26][CH2:25][CH:24]([C:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[NH:29][CH:28]=2)[CH2:23][CH2:22]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CC(C)CC(=O)C>[NH:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:27]([CH:24]2[CH2:25][CH2:26][N:21]([CH2:2][CH2:3][N:4]3[C:13](=[O:14])[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[N:6]=[C:5]3[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:22][CH2:23]2)=[CH:28]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 7022353-(4-Piperidinyl)-1H-indoleHCID 27720803-(2-chloroethyl)-2-phenylquinazolin-4(3H)-one

Product 1

HCID 134765303-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-2-phenyl-4(3H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 5.5 parts of 3-(2-chloroethyl)-2-phenyl-4(3H)-quinazolinone, 3.2 parts of 3-(4-piperidinyl)-1H-indole, 7 parts of sodium carbonate, 0.1 parts of potassium iodide and 200 parts of 4-methyl-2-pentanone is stirred and refluxed for 22 hours. The reaction mixture is filtered over Hyflo and the filtrate is evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (92:8 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from a mixture of ethanol and 1,1'-oxybisethane, yielding 5 parts of 3-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-2-phenyl-4(3H)-quinazolinone; mp. 191.3° C.

Workup

  1. temperaturerefluxed for 22 hours
  2. filtrationThe reaction mixture is filtered over Hyflo
  3. customthe filtrate is evaporated
  4. customThe residue is purified by column-chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol (92:8 by volume) as eluent
  6. customThe pure fractions are collected
  7. customthe eluent is evaporated
  8. customThe residue is crystallized from a mixture of ethanol and 1,1'-oxybisethane

Sources & evidence

ORD record
ord-442b15529d2248739b77604f734435b7
Source dataset
uspto-grants-1985_06
Patent number
US04522945

Reaction notes

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