Triethylamine → 2-{1-(1-Ethyl-1H-tetrazol-5-yl)piperidin-4-yl}ethanol

HRID 445083Notes

Reaction equation

HRID 445083 reaction equation
[CH2:1]([NH:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][OH:14])[CH2:8][CH2:7]1)=S)[CH3:2].[N-:15]=[N+:16]=[N-:17].[Na+].CCN(CC)CC>CN(C=O)C.Cl[Hg]Cl>[CH2:1]([N:3]1[C:4]([N:6]2[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][OH:14])[CH2:8][CH2:7]2)=[N:17][N:16]=[N:15]1)[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 33557Sodium AzideHCID 57850772HCID 57850772, compound

Product 1

HCID 685204702-{1-(1-Ethyl-1H-tetrazol-5-yl)piperidin-4-yl}ethanolYield 41%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of N-Ethyl-4-(2-hydroxyethyl)piperidine-1-carbothioamide (200 mg, 0.93 mmol), HgCl2 (277 mg, 1.02 mmol), and NaN3 (181 mg, 2.78 mmol) in DMF (2.5 mL) was added NEt3 (388 μL, 2.78 mmol) at rt. After stirring for 10 h, the reaction mixture was filtered, and the filter cake was washed with CH2Cl2. The combined filtrates and washings were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo, and the residue was purified by SiO2 chromatograph (60% EtOAc/hexane) to afford the titled compound (85 mg, 41%): 1H NMR (CDCl3) δ 4.18 (q, J=7.2 Hz, 2H), 3.75 (td, J=6.8, 5.2 Hz, 2H), 3.51 (brd, J=12.4, 2H), 3.03 (td, J=12.4, 2.8 Hz, 2H), 1.84 (brd, J=14.4 Hz, 2H), 1.71 (m, 1H), 1.59 (q, J=6.8 Hz, 2H), 1.56 (t, J=7.2 Hz, 3H), 1.48-1.38 (m, 2H)

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe filter cake was washed with CH2Cl2
  3. washThe combined filtrates and washings were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customthe residue was purified by SiO2 chromatograph (60% EtOAc/hexane)

Sources & evidence

ORD record
ord-89a6e4a4a5f64a78a32afc833c8fd1a2
Source dataset
uspto-grants-2013_07
Patent number
US08476285B2

Reaction notes

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