Ammonia → 1-(Pyrid-2-oyl)-3-[1-(naphth-2-ylmethyl)piperid-4-yl]urea

HRID 248905

Reaction equation

HRID 248905 reaction equation
[Na].N.[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([NH:20][C:21]([NH2:23])=[O:22])[CH2:16][CH2:15]1.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30](OCC)=[O:31]>>[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]([NH:23][C:21]([NH:20][CH:17]1[CH2:18][CH2:19][N:14]([CH2:13][C:4]2[CH:5]=[CH:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:3]=2)[CH2:15][CH2:16]1)=[O:22])=[O:31]

Participants

5

Reactant 4

HCID 222Ammonia3×HCID 17307Ethyl 2-pyridinecarboxylateHCID 5360545SodiumHCID 13145794[1-(Naphth-2-ylmethyl)piperid-4-yl]urea

Product 1

HCID 197623981-(Pyrid-2-oyl)-3-[1-(naphth-2-ylmethyl)piperid-4-yl]ureaYield 32.5%

Procedure

Sodium (0.1 g, 4.35 mmol) in liquid ammonia (100-150 cm3) was stirred until the blue colour was discharged. A bomb was charged with [1-(naphth-2-ylmethyl)piperid-4-yl]urea (0.83 g, 2.93 mmol) and the liquid ammonia solution was added. The mixture was stirred at room temperature for 2 days then the bomb was cooled to -78° C., and ethyl picolinate (0.6 g, 3.97 mmol) was added. Stirring was continued for 3 hours at room temperature then the ammonia was allowed to evaporate and the gummy residue triturated with water then ethyl acetate. The ethyl acetate suspension was filtered to give recovered [1-(naphth-2-ylmethyl)piperid-4-yl]urea (0.33 g). The filtrate was evaporated and the residue chromatographed on silica eluting with chloroform then chloroform: ethyl acetate 4:1 to give the title compound (0.37 g).

Workup

  1. temperaturethe bomb was cooled to -78° C.
  2. stirringStirring
  3. waitwas continued for 3 hours at room temperature
  4. customto evaporate
  5. customthe gummy residue triturated with water
  6. filtrationThe ethyl acetate suspension was filtered
  7. customto give
  8. customrecovered [1-(naphth-2-ylmethyl)piperid-4-yl]urea (0.33 g)
  9. customThe filtrate was evaporated
  10. customthe residue chromatographed on silica eluting with chloroform

Sources & evidence

ORD record
ord-e71edb4f34674b9db43252afc220840c
Source dataset
uspto-grants-1993_05
Patent number
US05212179

Linked notes

Loading…