Hydrochloric Acid → 5-methyl-2-(4-piperidinyl)methyl-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one dihydrochloride

HRID 1162328Notes

Reaction equation

HRID 1162328 reaction equation
[CH3:1][C:2]1[N:6]2[C:7](=[O:24])[N:8]([CH2:10][CH:11]3[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]3)[CH2:9][C:5]2=[CH:4][N:3]=1.[ClH:25]>C(O)C>[ClH:25].[ClH:25].[CH3:1][C:2]1[N:6]2[C:7](=[O:24])[N:8]([CH2:10][CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[CH2:9][C:5]2=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23138425tert-butyl 4-((5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)methyl)-1-piperidinecarboxylate

Product 1

HCID 231381375-methyl-2-(4-piperidinyl)methyl-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one dihydrochlorideYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To tert-butyl 4-((5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)methyl)-1-piperidinecarboxylate (3.5 g) obtained in Example 85a) was added concentrated hydrochloric acid (10 ml), and mixed for 10 minutes. To the reaction mixture was added ethanol, and the solvent was distilled off under reduced pressure. To the residue was further added ethanol, and the solvent was distilled off under reduced pressure. To the residue was added isopropyl alcohol, and the precipitate was collected by filtration. The precipitate was washed sequentially with isopropyl alcohol and diethyl ether and dried under reduced pressure to obtain 5-methyl-2-(4-piperidinyl)methyl-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one dihydrochloride as a colorless solid (2.5 g, 78%).

Workup

  1. additionmixed for 10 minutes
  2. distillationthe solvent was distilled off under reduced pressure
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionTo the residue was added isopropyl alcohol
  5. filtrationthe precipitate was collected by filtration
  6. washThe precipitate was washed sequentially with isopropyl alcohol and diethyl ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-3c01014afba649549ba72d67538716f5
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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