Hydrochloric Acid → HCID 178420312, compound

HRID 414233Notes

Reaction equation

HRID 414233 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([N:12]1[CH2:17][CH2:16][C:15]([C:25]#[N:26])([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Al+3].[Cl-].[Cl-].[Cl-].Cl.[OH-].[Na+]>C1COCC1>[CH2:5]([N:12]1[CH2:13][CH2:14][C:15]([C:25]2[NH:26][N:3]=[N:2][N:1]=2)([NH:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:16][CH2:17]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 704124-Anilino-1-benzylpiperidine-4-carbonitrileHCID 6451240Aluminum(III) Chloride

Product 1

HCID 178420312HCID 178420312, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium azide (5.85 g, 90 mmol) and 1-benzyl-4-cyano-4-anilinopiperidine (2.91 g, 10 mmol) were added slowly to a solution of AlCl3 (2.67 g, 20 mmole) in dry THF (100 ml). The resulting mixture was refluxed overnight. The reaction was quenched with water (50 ml). After separating the THF layer, the aqueous layer was extracted with additional THF (4×50 ml). The combined THF layers were dried over MgSO4 and concentrated in vacuo. The solid obtained was dissolved in 1N.HCl solution and the pH was adjusted to 6.0 with 1N NaOH solution. The resulting mixture was left overnight and filtered to give the product (1.58 g, 4.7 mmol) as white crystalline solid: mp 205°-206° C. (decomposed); IR (nujol) 3300 cm-1 ; NMR (270 MHz, DMSO-d6) δ2.2 to 2.7 (m, 8H, piperidine CH2), 3.53 (s, 2H, benzyl CH2), 6.35, 6.63 and 7.01 (3m, 5H, anilinophenyl H's), 7.25 (m, 5H, benzylphenyl H's). Anal. Calcd. for C19H22N6 : C, 68.24; H, 6.63; N, 25.13. Found: C, 68.79; H, 6.76; N, 24.81. ##STR22##

Workup

  1. temperatureThe resulting mixture was refluxed overnight
  2. customThe reaction was quenched with water (50 ml)
  3. customAfter separating the THF layer
  4. extractionthe aqueous layer was extracted with additional THF (4×50 ml)
  5. dry with materialThe combined THF layers were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe solid obtained
  8. dissolutionwas dissolved in 1N
  9. filtrationfiltered

Sources & evidence

ORD record
ord-e8b285f006dd4887a884c363b4ce3d86
Source dataset
uspto-grants-1988_12
Patent number
US04791120

Reaction notes

Loading…