Ammonium Hydroxide → N-Hydroxy-N-[4-(4-oxo-1-piperidineyl)benzyl]urea

HRID 1061227Notes

Reaction equation

HRID 1061227 reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:22]=[CH:21][C:14]([CH2:15][N:16]([OH:20])[C:17]([NH2:19])=[O:18])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4]CC1.[OH-].[NH4+]>Cl>[OH:20][N:16]([CH2:15][C:14]1[CH:13]=[CH:12][C:11]([N:8]2[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]2)=[CH:22][CH:21]=1)[C:17]([NH2:19])=[O:18]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 12965961N-[4-(1,4-Dioxa-8-azaspiro[4.5]dec-8-yl)benzyl]-N-hydroxyurea

Product 1

HCID 12965962N-Hydroxy-N-[4-(4-oxo-1-piperidineyl)benzyl]ureaYield 98.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of N-[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)benzyl]-N-hydroxyurea (2.2 g, 7.16 mmol) (which was obtained in Example 53) and hydrochloric acid (concentrated, 10 mL) was stirred at room temperature for three days. The mixture was then neutralized with ammonium hydroxide, and extracted with ethyl acetate. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (ethyl acetate) gave a white solid (1.86 g, 98% yield); mp 138-140° C.; 1H NMR (300 MHz, DMSO-d6) δ 2.41 (m, 4H), 3.60 (m, 4H), 4.43 (s, 2H), 6.37 (brs, 2H), 7.03 (m, 2H), 7.21 (m, 2H), 9.31 (s, 1H); MS (ES) m/z: 264 (MH+);

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic extracts were dried over MgSO4
  3. customEvaporation and purification by flash chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-5a382817d9e64fbb85c04133532be049
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

Loading…