Methane → N-[[[1-[(6-Fluoro-2-naphthalenyl)methyl]-4-piperidinyl]amino]carbonyl]-4-pyridinecarboxamide

HRID 703858Notes

Reaction equation

HRID 703858 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([F:19])[CH:15]=3)[CH:10]=2)[CH2:4][CH2:3]1.[N:20]1[CH:25]=[CH:24][C:23]([C:26]([NH:28][C:29](N)=[O:30])=[O:27])=[CH:22][CH:21]=1.N1C=CC=CC=1.C>O.C(Cl)(Cl)Cl>[F:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([CH2:8][N:5]1[CH2:6][CH2:7][CH:2]([NH:1][C:29]([NH:28][C:26]([C:23]3[CH:22]=[CH:21][N:20]=[CH:25][CH:24]=3)=[O:27])=[O:30])[CH2:3][CH2:4]1)[CH:18]=[CH:17]2

Participants

7

Reactant 4

HCID 297MethaneHCID 1049PyridineHCID 594347Piperidin-4-amine, 1-(6-fluoro-2-naphthylmethyl)-HCID 13851072Isonicotinoyl Urea

Product 1

HCID 13851073N-[[[1-[(6-Fluoro-2-naphthalenyl)methyl]-4-piperidinyl]amino]carbonyl]-4-pyridinecarboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 4-amino-1-[(6-fluoro-2-naphthalenyl)methyl]piperidine (1.3 g, 5 mmol), 4-pyridoylurea (0.9 g, 5 mmol) and pyridine (6 ml) was stirred at reflux for 16 hours. The solution was diluted with water (8 ml) and the precipitated dark brown product collected by filtration to give 1.5 g. The crude product was dissolved in chloroform (25 ml), shaken with decolourising charcoal, filtered and evaporated. The residue was suspended in hot ethanol (20 ml) and succinic acid (0.44 g) added to give a clear solution which crystallised on standing. The product crystals were collected by filtration and washed with ethanol to give the succinate salt of the title compound. m.p. 187°-188° C.

Workup

  1. temperatureat reflux for 16 hours
  2. filtrationthe precipitated dark brown product collected by filtration
  3. customto give 1.5 g
  4. filtrationfiltered
  5. customevaporated
  6. additionsuccinic acid (0.44 g) added
  7. customto give a clear solution which
  8. customcrystallised
  9. filtrationThe product crystals were collected by filtration
  10. washwashed with ethanol

Sources & evidence

ORD record
ord-945c522e0d024e1d9b970fadf45a01c1
Source dataset
uspto-grants-1991_01
Patent number
US04985438

Reaction notes

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