Potassium Iodide → N-(4-(1H-benzotriazole-1-yl)butyl)-4-(1-naphthyl)piperidine

HRID 1482641Notes

Reaction equation

HRID 1482641 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[N:7]1.[C:15]1([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.C(N(C(C)C)CC)(C)C.[I-].[K+]>C(#N)C>[N:6]1([CH2:5][CH2:4][CH2:3][CH2:2][N:28]2[CH2:29][CH2:30][CH:25]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17][CH:16]=3)[CH2:26][CH2:27]2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[N:7]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 34251071-(4-chlorobutyl)-1H-benzotriazoleHCID 148193164-(Naphthalen-1-YL)piperidine

Product 1

HCID 76281932N-(4-(1H-benzotriazole-1-yl)butyl)-4-(1-naphthyl)piperidineYield 60.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(4-chlorobutyl)-1H-benzotriazole (7.55 g, 0.036 mol) was dissolved into 100 ml of acetonitrile, 4-(1-naphthyl)piperidine (6.4 g, 0.03 mol), diisopropylethylamine (15.5 g, 0.12 mol) and potassium iodide (5.0 g, 0.03 mol) were respectively added. The mixture was stirred and mixed, then heated and refluxed to react for 20 hours. The mixture was cooled down to ambient temperature and filtered. The filtrate was concentrated to produce oily products, and treated by chromatography with neutral Al2O3 and purified, eluted with dichloromethane to produce 6.9 g compound (I-122) with a yield of 60.1%. ESI-MS [M+H]+: m/z 385.3.

Workup

  1. additionwere respectively added
  2. additionmixed
  3. temperatureheated
  4. temperaturerefluxed
  5. customto react for 20 hours
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customto produce oily products
  9. additiontreated by chromatography with neutral Al2O3
  10. custompurified
  11. washeluted with dichloromethane

Sources & evidence

ORD record
ord-d122b53c8f20415bb8946b685328c4f2
Source dataset
uspto-grants-2016_08
Patent number
US09415047B2

Reaction notes

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