4-Amino-1-(2-naphthyl)methylpiperidine → HCID 13853616, compound

HRID 868213Notes

Reaction equation

HRID 868213 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]=[CH:14][CH:15]=3)[CH:10]=2)[CH2:4][CH2:3]1.N[C:20]([NH:22][C:23]([C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[N:31]=[CH:30][CH:29]=[CH:28]2)=[O:24])=[O:21]>N1C=CC=CC=1>[CH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[CH:18][C:9]=1[CH2:8][N:5]1[CH2:4][CH2:3][CH:2]([NH:1][C:20]([NH:22][C:23]([C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[N:31]=[CH:30][CH:29]=[CH:28]3)=[O:24])=[O:21])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 111958234-Amino-1-(2-naphthyl)methylpiperidine2×HCID 13853615HCID 13853615, compound

Product 1

HCID 13853616HCID 13853616, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A suspension of 4-amino-1-(2-naphthalenylmethyl)piperidine (1.4 g, 5.83 mmol) and N-aminocarbonyl-6-quinolinecarboxamide (1.08 g, 5.02 mmol) in pyridine (7 cm3) was refluxed for 7 hours. The mixture was left at room temperature overnight then more 4-amino-1-(2-naphthalenylmethyl)piperidine (0.3 g, 1.4 mmol) was added and refluxing was continued for 5 hours. Undissolved solid was filtered off from the hot mixture and the filtrate was diluted with water (8 cm3) and filtered again. The filtrate was further diluted with water and cooled in ice. The deposited solid was collected and dried (0.46 g,) then recrystallised from ethanol (50 cm3) to give 0.30 g of the title compound, m.p. 211°-13° C.

Workup

  1. temperaturewas refluxed for 7 hours
  2. temperaturerefluxing
  3. waitwas continued for 5 hours
  4. filtrationwas filtered off from the hot mixture
  5. additionthe filtrate was diluted with water (8 cm3)
  6. filtrationfiltered again
  7. additionThe filtrate was further diluted with water
  8. temperaturecooled in ice
  9. customThe deposited solid was collected
  10. customdried (0.46 g,)
  11. customthen recrystallised from ethanol (50 cm3)

Sources & evidence

ORD record
ord-cdc02c044beb43e1a341372b46e39559
Source dataset
uspto-grants-1988_10
Patent number
US04778802

Reaction notes

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