Hydrochloric Acid → 2,4-Dioxo-1-[(5-methyl-1H-imidazol-4-yl)methyl]piperidine

HRID 2379145Notes

Reaction equation

HRID 2379145 reaction equation
C[O:2][C:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[N:11]=[CH:12][N:13](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:14]=2[CH3:15])[C:5](=[O:35])[CH:4]=1.Cl>C1COCC1>[O:35]=[C:5]1[CH2:4][C:3](=[O:2])[CH2:8][CH2:7][N:6]1[CH2:9][C:10]1[N:11]=[CH:12][NH:13][C:14]=1[CH3:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 104345435,6-Dihydro-4-methoxy-1-[[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]-2(1H)-pyridinone

Product 1

HCID 156163172,4-Dioxo-1-[(5-methyl-1H-imidazol-4-yl)methyl]piperidineYield 62.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5,6-dihydro-4-methoxy-1-[[5-methyl-1-(triphenylmethyl)-1H-imidazol-4yl]methyl]-2(1H)-pyridinone (500 mg) in THF (4 ml) was added hydrochloric acid (5M; 1 ml), and the mixture was stirred at 50° for 1 h. The solvent was removed in vacuo, triethylamine (1 ml) was added, and the mixture was again evaporated to dryness. FCC of the residue eluting with ethyl acetate:methanol:triethylamine (8:4:1) gave the title compound (139 mg), m.p. 100°-106° (decomp.).

Workup

  1. customThe solvent was removed in vacuo, triethylamine (1 ml)
  2. additionwas added
  3. customthe mixture was again evaporated to dryness
  4. washFCC of the residue eluting with ethyl acetate:methanol:triethylamine (8:4:1)

Sources & evidence

ORD record
ord-18f0171ecee64e82bf5ea7a4d799337b
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

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