Triethylamine hydrochloride → HCID 178469255, compound

HRID 1963237Notes

Reaction equation

HRID 1963237 reaction equation
[C:1]([CH:3]1[CH2:8][CH:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][CH2:5][N:4]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])#[N:2].[N-:24]=[N+:25]=[N-:26].[Na+].Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1>[NH:24]1[C:1]([CH:3]2[CH2:8][CH:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][CH2:5][N:4]2[C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])=[N:2][N:26]=[N:25]1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 59536567HCID 59536567, compound

Product 1

HCID 178469255HCID 178469255, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

1-Benzyl 4-ethyl 2-cyanopiperidine-1,4-dicarboxylate (2.5 g, 7.90 mmol) was dissolved in toluene (50 mL) and sodium azide (0.822 g, 12.64 mmol) and triethylamine hydrochloride (1.740 g, 12.64 mmol) were added and the mixture was heated at 95° C. overnight. The reaction mixture was allowed to cool to room temperature and was washed with 2 M HCl. The aqueous phase was extracted with EtOAc and the combined organic phase was dried over Na2SO4 and evaporated to yield 1-benzyl 4-ethyl 2-(1H-tetrazol-5-yl)piperidine-1,4-dicarboxylate (2.8 g, 99%). MS m/z 360 (M+H)+

Workup

  1. temperatureto cool to room temperature
  2. washwas washed with 2 M HCl
  3. extractionThe aqueous phase was extracted with EtOAc
  4. dry with materialthe combined organic phase was dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-61a8c7bc816345bfb33163c9358e28b1
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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