Hydrochloric Acid → HCID 178420312, compound

HRID 2350917Notes

Reaction equation

HRID 2350917 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 (3 m, 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. ##STR20##

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-ddda0ad1d3ec47e8bc08e1c50b79bf6f
Source dataset
uspto-grants-1989_10
Patent number
US04871749

Reaction notes

Loading…