4-Phenylpiperidine → HCID 19789520, compound

HRID 1655850Notes

Reaction equation

HRID 1655850 reaction equation
[I-:1].[NH2:2][C:3]1[N:8]=[C:7](Cl)[CH:6]=[C:5]([CH3:10])[N+:4]=1[CH3:11].[C:12]1([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)C>[I-:1].[NH2:2][C:3]1[N:8]=[C:7]([N:21]2[CH2:22][CH2:23][CH:18]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:19][CH2:20]2)[CH:6]=[C:5]([CH3:10])[N+:4]=1[CH3:11]

Participants

4

Reactant 2

HCID 698734-PhenylpiperidineHCID 12317609HCID 12317609, compound

Product 1

HCID 19789520HCID 19789520, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-4-chloro-1,6-dimethylpyrimidinium iodide (0.571 g; 2 mM; described in Indian Research, 1976, 21 p. 96) and 4-phenylpiperidine (0.644 g; 4 mM) in ethanol (30 ml) was heated under reflux for 15 hours. The solvent was removed in vacuo and the residue was triturated with ether. The solid was removed by filtration and recrystallised from a mixture of methanol and ether to give 2-amino-1,6-dimethyl-4-(4-phenylpiperidino)pyrimidinium iodide as a solid (0.41 g, 50% yield), m.p. 248°-250° C. (decomp.); microanalysis, found: C,50.0; H,5.6; N,13.7%; C17H23N4I requires C,49.8; H,5.6; N,13.7%; NMR (220 MHz; d5): 1.4-1.75 (2H, b, piperidine 3-H axial and 5-H axial), 1.85-2.0 (2H, d, piperidine 3-H equatorial and 5-H equatorial), 2.4 (3H, s, CH3), 2.8-3.3 (3H, b, piperidine 4-H and piperidine 2-H axial and 6-H axial), 3.45 (3H, s, N--CH3), 4.2-4.4 (1H, broad d, piperidine 2-H equatorial or 6-H equatorial), 4.85-5.05 (1H, broad d, piperidine 6-H equatorial or 2-H equatorial), 6.7 (1H, s pyrimdine 5H), 7.1-7.4 (5H, complex, aromatic H), 7.85-8.0 (2H, br, NH2).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue was triturated with ether
  5. customThe solid was removed by filtration
  6. customrecrystallised from a mixture of methanol and ether

Sources & evidence

ORD record
ord-562435d6591147c59c97e771d1bf596e
Source dataset
uspto-grants-1993_10
Patent number
US05252567

Reaction notes

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