Triethylamine hydrochloride → HCID 178452097, compound

HRID 59794Notes

Reaction equation

HRID 59794 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][CH2:7][N:8]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=2)[CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[N-:33]=[N+:34]=[N-:35].[Na+].Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1>[NH:33]1[C:29]([C:25]2[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=2)[CH2:22][N:8]([CH2:7][CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:32][CH:31]=2)[CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]2)=[N:30][N:35]=[N:34]1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 121422691HCID 121422691, compound

Product 1

HCID 178452097HCID 178452097, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-Butyl 4-((4-chlorophenethyl)(3-cyanobenzyl)amino)piperidine-1-carboxylate obtained in Step 1 was dissolved in toluene (5 mL/mmol) and sodium azide (3 equiv) and triethylamine hydrochloride (0.1 equiv) were added to this solution. The heterogeneous mixture was refluxed for 3 days after which time the starting material could no longer be detected. After cooling down to ambient temperature the solids were filtered off and the solvent was stripped off in vacuo. The crude product was purified by silica gel chromatography (yield 60%).

Workup

  1. temperatureThe heterogeneous mixture was refluxed for 3 days after which time the starting material
  2. filtrationwere filtered off
  3. customThe crude product was purified by silica gel chromatography (yield 60%)

Sources & evidence

ORD record
ord-3dd5ba43fbda492689f6d4144338c0a8
Source dataset
uspto-grants-2016_09
Patent number
US09440953B2

Reaction notes

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