Potassium Iodide → alpha,alpha-Diphenyl-1-[3-(8-quinolinyloxy)propyl]-3-piperidinepropanenitrile hemihydrate

HRID 1193710Notes

Reaction equation

HRID 1193710 reaction equation
[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:29]=[CH:30][CH:31]=[C:32]2[C:37]=1[N:36]=[CH:35][CH:34]=[CH:33]2.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(O)CCC.C(Cl)(Cl)Cl.CO.C(OCC)(=O)C>[OH2:27].[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][N:13]([CH2:24][CH2:25][CH2:26][O:27][C:28]3[CH:29]=[CH:30][CH:31]=[C:32]4[C:37]=3[N:36]=[CH:35][CH:34]=[CH:33]4)[CH2:12]2)[C:8]#[N:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][N:13]([CH2:24][CH2:25][CH2:26][O:27][C:28]3[CH:29]=[CH:30][CH:31]=[C:32]4[C:37]=3[N:36]=[CH:35][CH:34]=[CH:33]4)[CH2:12]2)[C:8]#[N:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 13295785HCID 13295785, compoundHCID 14407190alpha,alpha-Diphenyl-3-piperidinepropanenitrile

Product 1

HCID 88630242alpha,alpha-Diphenyl-1-[3-(8-quinolinyloxy)propyl]-3-piperidinepropanenitrile hemihydrate

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 6212ChloroformSolventHCID 21584119Ethylacetate methanolSolvent3×

Procedure

A mixture of α,α-diphenyl-3-piperidinepropanenitrile (8.12 g, 0.028 mole), 8-(3-chloropropoxy)quinoline (6.18 g, 0.028 mole), and potassium carbonate (5.53 g, 0.04 mole) was heated at reflux overnight in 350 ml of 1-butanol containing potassium iodide (0.3 g). The reaction was filtered and stripped to dryness on a rotary evaporator. The residue obtained was dissolved in chloroform and extracted with 5% sodium hydroxide and water. The chloroform layer was dried over anhydrous sodium sulfate, filtered, and solvent removed to give a dark red mass. This material was subjected to flash chromatography on a silica gel column using 10% methanol-ethyl acetate, 20% methanol-ethyl acetate, and 50% methanol-ethyl acetate for elution. Fractions of similar purity were combined and solvent was removed by rotary evaporator. The red black residue obtained was dried in vacuo at 80° C. overnight. This furnished 5.29 g (39%) of a dark black residue. 1H NMR (CDCl3): σ 8.9 (m, 1, proton ortho to N in ring), 7.9-8.1 (m, l, proton para to N in ring), 6.9-7.6 (m, 14, aromatics), 4.2 (t, 2, methylenes adjacent to oxygen atom), 1.1-2.7 (m, 16, aliphatic portons and 1H from 0.5 H2O).

Workup

  1. temperaturewas heated
  2. filtrationThe reaction was filtered
  3. customstripped to dryness on a rotary evaporator
  4. customThe residue obtained
  5. extractionextracted with 5% sodium hydroxide and water
  6. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customsolvent removed
  9. customto give a dark red mass
  10. washfor elution
  11. customsolvent was removed by rotary evaporator
  12. customThe red black residue obtained
  13. customwas dried in vacuo at 80° C. overnight

Sources & evidence

ORD record
ord-8641a2b05c8243f0b6f9342de270b10d
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

Loading…