Triethylamine → HCID 68520470, compound

HRID 736659Notes

Reaction equation

HRID 736659 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 68520470HCID 68520470, compoundYield 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-ad42355454114efb93827523b9dd0844
Source dataset
uspto-grants-2009_09
Patent number
US07595401B2

Reaction notes

Loading…