Sodium Carbonate → 4-(2-Bromo-5-fluorophenoxy)-N'-hydroxypiperidine-1-carboximidamide

HRID 561214Notes

Reaction equation

HRID 561214 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]#[N:12])[CH2:7][CH2:6]1.Cl.[NH2:19][OH:20].C([O-])([O-])=O.[Na+].[Na+]>CCO.O>[Br:1][C:2]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11](=[N:19][OH:20])[NH2:12])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 86620459HCID 86620459, compound

Product 1

HCID 866204604-(2-Bromo-5-fluorophenoxy)-N'-hydroxypiperidine-1-carboximidamide

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(2-bromo-5-fluorophenoxy)piperidine-1-carbonitrile (1.6 g, 5.3 mmol), hydroxylamine hydrochloride (1.1 g, 16.1 mmol) and Na2CO3 (2.3 g, 92 mmol) in EtOH/water 4:1 (26 ml) was heated at 80° C. for 1 h. The solvent was evaporated. The residue was acidified with 6N HCl and washed with Et2O (2×10 mL). The aqueous layer was made basic with solid Na2CO3 and extracted with EtOAc (3×20 mL). The combined organic fractions were dried over Na2SO4 and the solvent was evaporated under reduced pressure to give the title compound as a foam which was used in the next step without further purification. MS: m/z 332, 334 (MH+).

Workup

  1. customThe solvent was evaporated
  2. washwashed with Et2O (2×10 mL)
  3. extractionextracted with EtOAc (3×20 mL)
  4. dry with materialThe combined organic fractions were dried over Na2SO4
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-075f360ecd7340c1ab84b9f25ac4cd31
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

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