Hydrogen Sulfide → HCID 14955099, compound

HRID 1683331Notes

Reaction equation

HRID 1683331 reaction equation
[CH3:1][CH:2]([CH3:12])[CH2:3][N:4]1[CH2:9][CH2:8][C:7]([CH3:11])([CH3:10])[CH2:6][CH2:5]1.S>C(O)(=O)C>[CH3:1][CH:2]([CH3:12])[CH2:3][N:4]1[CH2:9][CH2:8][C:7]([CH3:10])([CH3:11])[CH:6]=[CH:5]1

Participants

4

Reactant 2

HCID 402Hydrogen SulfideHCID 19043493HCID 19043493, compound

Product 1

HCID 14955099HCID 14955099, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1-(2-Methylpropyl)-4,4-dimethylpiperidine (13.0 g, 0.077 mol) and mercuric acetate (98.8 g, 0.31 mol, 4 molar equivalent) in 5% aqueous acetic acid (300 ml) was boiled for 2.5 hours. On cooling, the white solid (mercurous acetate) was filtered-off, and the filtrate was treated repeatedly with hydrogen sulphide gas (3×), each time the mixture was filtered through a celite pad, the final filtrate made basic to pH 10 with K2CO3. The aqueous layer was extracted with ether (3×100 ml), and the combined organic layers dried over anhydrous MgSO4, concentrated and distilled to give the product, 1-(2-methylpropyl)-4,4-dimethyl-1,4,5,6-tetrahydropyridine, 7.1 g (55%), b.p. 50°-53° C. (2 mmHg). 1HNMR (CDCl3) δ5.73 (IH, d), 4.05 (1H, d), 2.88 (2H, t), 2.55 (2H, d), 1.80 (1H, m), 1.55 (2H, t), 0.95 (6H, s), and 0.85 (6H, d).

Workup

  1. temperatureOn cooling
  2. filtrationeach time the mixture was filtered through a celite pad
  3. extractionThe aqueous layer was extracted with ether (3×100 ml)
  4. dry with materialthe combined organic layers dried over anhydrous MgSO4
  5. concentrationconcentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-3daab933cc954dd994cdb4428821ee1f
Source dataset
uspto-grants-1997_06
Patent number
US05637718

Reaction notes

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