Methyl iodide → 1,2-Dimethyl-6-methylamino-4-(4-phenylpiperidino)pyrimidinium iodide

HRID 1655848Notes

Reaction equation

HRID 1655848 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([NH:20][CH3:21])[N:3]=1.[CH3:22][I:23]>O1CCOCC1>[I-:23].[CH3:22][N+:3]1[C:4]([NH:20][CH3:21])=[CH:5][C:6]([N:8]2[CH2:9][CH2:10][CH:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH2:13]2)=[N:7][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 197895132-Methyl-6-methylamino-4-(4-phenylpiperidino)pyrimidine

Product 1

HCID 197895151,2-Dimethyl-6-methylamino-4-(4-phenylpiperidino)pyrimidinium iodideYield 60%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-methyl-6-methylamino-4-(4-phenylpiperidino)pyrimidine (564 mg; 2 mM) and methyl iodide (1 ml; 16 mM) in dioxan (10 ml) was heated under reflux for 15 hours. The mixture was cooled, the solvent removed in vacuo and the residue was crystallised from a mixture of methanol and ether. There was thus obtained 1,2-dimethyl-6-methylamino-4-(4-phenylpiperidino)pyrimidinium iodide (506 mg, 60% yield) m.p. 193°-196° C.; microanalysis found: C,50.6; H,5.8; N,12.9%; C18H25N4I reqiures C,50.9; H,5.9; N,13.2%; NMR (200 MHz, d6 -DMSO): 1.45-1.75 (2H, octet, piperidine 3-H axial and 5-H axial), 1.85-2.00 (2H,d, piperidine 3-H equatorial and 5-H equatorial), 2.55-2.60 (3H,s, CH3), 2.85-2.95 (3H, d, NHCH3), 3.00-3.20 (3H, br, piperidine 2-H axial and 6-H axial), 3.45-3.55 (3H, s, N--CH3), 4.4-4.8 (2H, br, piperidine 2-H equatorial and 6-H equatorial), 5.8-5.85 (1H, s, pyrimidine 5-H), 7.15-7.40 (5H, complex, aromatic), 7.7-7.85 (1H,q, NH).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. temperatureThe mixture was cooled
  4. customthe solvent removed in vacuo
  5. customthe residue was crystallised from a mixture of methanol and ether

Sources & evidence

ORD record
ord-0c8ab4e82dc949ac9be2b56231fe51ca
Source dataset
uspto-grants-1993_10
Patent number
US05252567

Reaction notes

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