Hydrochloric Acid → (S)-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]amine dihydrochloride

HRID 856345Notes

Reaction equation

HRID 856345 reaction equation
[CH3:1][C@@:2]1([CH2:13][N:14]2[CH2:19][CH2:18][N:17]([NH:20]C(=O)OC(C)(C)C)[CH2:16][CH2:15]2)[O:6][C:5]2=[N:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][N:4]2[CH2:3]1.[ClH:28]>CO>[ClH:28].[ClH:28].[CH3:1][C@@:2]1([CH2:13][N:14]2[CH2:19][CH2:18][N:17]([NH2:20])[CH2:16][CH2:15]2)[O:6][C:5]2=[N:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][N:4]2[CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86760538tert-butyl(S)-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]carbamate

Product 1

HCID 69479768(S)-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]amine dihydrochlorideYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of tert-butyl (S)-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)-piperazin-1-yl]carbamate prepared in Example 503 (300 mg, 0.78 mmol), concentrated hydrochloric acid (2 ml) and methanol (4 ml) was stirred at 50° C. for 30 minutes. The reaction mixture was allowed to return to room temperature and concentrated under reduced pressure. The residue was recrystallized from methanol/ether to afford (S)-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]amine dihydrochloride (265 mg, yield 91%) as a yellow powder.

Workup

  1. customto return to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was recrystallized from methanol/ether

Sources & evidence

ORD record
ord-53f8b5a20d0541d187d87783bf07711b
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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