Piperidine → 1-(4-Hexadecylamino-2-thiophenecarbonyl)piperidine

HRID 850987Notes

Reaction equation

HRID 850987 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.Cl.[CH2:24]([NH:40][C:41]1[CH:42]=[C:43]([C:46](Cl)=[O:47])[S:44][CH:45]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>CCOCC>[CH2:24]([NH:40][C:41]1[CH:42]=[C:43]([C:46]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:47])[S:44][CH:45]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 205036504-Hexadecylamino-2-thiophenecarbonyl chloride hydrochloride

Product 1

HCID 205036111-(4-Hexadecylamino-2-thiophenecarbonyl)piperidine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a chilled solution of 35 ml. of piperidine, 2.5 ml. of triethylamine and 0.6 g. of dimethylaminopyridine in 100 ml. of diethyl ether is added (1/2 hour) a solution of 8.3 g. of 4-hexadecylamino-2-thiophenecarbonyl chloride hydrochloride in 50 ml. of ether. The solution is warmed to room temperature and maintained there for two hours. The solution is heated to reflux for an additional 2 hours at which time the reaction is complete. The solution is cooled, extracted twice with water and dried. The solvent is removed in vacuo and the solid is recrystallized from ether to yield the product as a white solid.

Workup

  1. temperaturemaintained there for two hours
  2. temperatureThe solution is heated
  3. temperatureto reflux for an additional 2 hours at which time the reaction
  4. temperatureThe solution is cooled
  5. extractionextracted twice with water
  6. customdried
  7. customThe solvent is removed in vacuo
  8. customthe solid is recrystallized from ether

Sources & evidence

ORD record
ord-a3bb02f5210c4453bea26f0161225774
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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