N-4-Piperidylbenzamide → HCID 12786448, compound

HRID 647597Notes

Reaction equation

HRID 647597 reaction equation
[C:1]([NH:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:17][CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]2[C:28]([CH3:33])=[N:29][CH:30]=[C:31]([CH3:32])[C:20]=12>C(Cl)(Cl)Cl>[CH3:33][C:28]1[N:21]2[C:22]3[C:27]([C:19]([CH2:18][CH2:17][N:13]4[CH2:14][CH2:15][CH:10]([NH:9][C:1](=[O:8])[C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)[CH2:11][CH2:12]4)=[C:20]2[C:31]([CH3:32])=[CH:30][N:29]=1)=[CH:26][CH:25]=[CH:24][CH:23]=3

Participants

4

Reactant 2

HCID 118120N-4-PiperidylbenzamideHCID 12708186HCID 12708186, compound

Product 1

HCID 12786448HCID 12786448, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

An intimate mixture of powdered 4-benzoylaminopiperidine (4.08 g) and 5-(2-chloroethyl)-1,4-dimethylpyrimido[1,6-a]indole (5.18 g. described in Example 12) is heated at 150°-160° C. for 30 minutes. After cooling, the melt is dissolved in chloroform, washed with 10% sodium hydroxide and repeatedly with water. The organic phase is dried over magnesium sulfate and evaporated. The residue is chromatographed on silica gel using chloroform-methanol (35:1). The eluates are evaporated and the residue is crystallized from ethanol-diethyl ether to give 4.15 g of the title compound, mp 233°-234° C. The title compound is coverted to the dihydrochloride salt and crystallized from methanol; mp 247° C.; ir (nujol) 3255, 2450 and 1625 cm-1 ; uv(MeOH) λmax 256, 297, 309 and 322 nm; ε=33700, 6000, 9050 and 10880, respectively.

Workup

  1. temperatureis heated at 150°-160° C. for 30 minutes
  2. temperatureAfter cooling
  3. washwashed with 10% sodium hydroxide and repeatedly with water
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. customevaporated
  6. customThe residue is chromatographed on silica gel
  7. customThe eluates are evaporated
  8. customthe residue is crystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-1723ac1ad0c945529acdab036b3046fa
Source dataset
uspto-grants-1983_10
Patent number
US04409224

Reaction notes

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