Ammonium Hydroxide → HCID 15751500, compound

HRID 1974625Notes

Reaction equation

HRID 1974625 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]([F:32])=[CH:16][C:17]3[N:21]=[C:20]([CH2:22][C:23]([O:25]CC)=O)[N:19]([CH:28]4[CH2:30][CH2:29]4)[C:18]=3[CH:31]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+:34].[OH-].[NH4+]>C(O)C>[C:23]([CH2:22][C:20]1[N:19]([CH:28]2[CH2:30][CH2:29]2)[C:18]2[CH:31]=[C:14]([N:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:13][CH2:12]3)[C:15]([F:32])=[CH:16][C:17]=2[N:21]=1)(=[O:25])[NH2:34]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 15751497HCID 15751497, compound

Product 1

HCID 15751500HCID 15751500, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 6-[4-(tert-butoxycarbonyl)-1-piperazinyl]-1-cyclopropyl-5-fluoro-2-benzimidazoleacetate (4.5 g, 10 mmol) is dissolved in ethanol (100 ml) and treated with ammonium chloride (5.35 g, 100 mmol) and 25 percent ammonium hydroxide solution (50 ml). The suspension obtained is stirred at 50° for 18 hours and thereafter evaporated under reduced pressure. The residue is suspended in ethyl acetate (150 ml) and the insoluble ammonium chloride is filtered off. The filtrate is concentrated to a volume of 50 ml and then chromatographed on silica gel (eluent: ethyl acetate/methanol 9:1). The product is recrystallized from ethyl acetate/n-hexane. There are obtained 2.22 g (53%) of tert-butyl 4-[2-(carbamoylmethyl)-1-cyclopropyl-5-fluoro-6-benzimidazolyl]-1-piperazinecarboxylate with a m.p. of 219°-220°.

Workup

  1. customThe suspension obtained
  2. customevaporated under reduced pressure
  3. filtrationthe insoluble ammonium chloride is filtered off
  4. concentrationThe filtrate is concentrated to a volume of 50 ml
  5. customchromatographed on silica gel (eluent: ethyl acetate/methanol 9:1)
  6. customThe product is recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-29930091b9d548acb763c494823021e4
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

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