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

HRID 1162358Notes

Reaction equation

HRID 1162358 reaction equation
[CH3:1][C:2]1[N:6]2[C:7](=[O:33])[N:8]([CH:10]3[CH2:15][CH2:14][N:13]([C:16](=[O:32])[CH:17]([NH:24]C(=O)OC(C)(C)C)[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:12][CH2:11]3)[CH2:9][C:5]2=[CH:4][N:3]=1.[ClH:34]>C(O)C>[ClH:34].[ClH:34].[NH2:24][CH:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:16]([N:13]1[CH2:14][CH2:15][CH:10]([N:8]2[CH2:9][C:5]3=[CH:4][N:3]=[C:2]([CH3:1])[N:6]3[C:7]2=[O:33])[CH2:11][CH2:12]1)=[O:32]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23138346tert-butyl 2-(4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)-2-oxo-1-phenylethylcarbamate

Product 1

HCID 231383382-(1-(2-amino-2-phenylacetyl)-4-piperidinyl)-5-methyl-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one dihydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl 2-(4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)-2-oxo-1-phenylethylcarbamate (13 g) obtained in Example 50a) was dissolved in concentrated hydrochloric acid (30 ml) and ethanol (30 ml). The reaction mixture was mixed at room temperature for 30 minutes, and then the solvent was distilled off under reduced pressure. Water in the residue was removed by azeotropy with ethanol to obtain the title compound as pale yellow powder (12 g, quantitative).

Workup

  1. additionThe reaction mixture was mixed at room temperature for 30 minutes
  2. distillationthe solvent was distilled off under reduced pressure
  3. customWater in the residue was removed by azeotropy with ethanol

Sources & evidence

ORD record
ord-f32132efc5eb41a2a372e6bb24d4dd36
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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