Piperidine → 1-[4-(16-Bromohexadecylamino)benzoyl]piperidine

HRID 1389654Notes

Reaction equation

HRID 1389654 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.[Br:24][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][CH2:39][CH2:40][NH:41][C:42]1[CH:50]=[CH:49][C:45]([C:46](Cl)=[O:47])=[CH:44][CH:43]=1>CCOCC>[Br:24][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][CH2:39][CH2:40][NH:41][C:42]1[CH:43]=[CH:44][C:45]([C:46]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:47])=[CH:49][CH:50]=1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 130254084-(16-Bromohexadecylamino)benzoyl chloride hydrochloride

Product 1

HCID 130254111-[4-(16-Bromohexadecylamino)benzoyl]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-(16-bromohexadecylamino)benzoyl 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 100 ml. portions of water and dried over magnesium sulfate. The solvent is removed in vacuo and the solid is recrystallized in 50 ml. of diethyl ether to yield the product.

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 100 ml
  6. dry with materialportions of water and dried over magnesium sulfate
  7. customThe solvent is removed in vacuo
  8. customthe solid is recrystallized in 50 ml
  9. customof diethyl ether to yield the product

Sources & evidence

ORD record
ord-1ae56a8d1f3b459ebcafbe33b86393dc
Source dataset
uspto-grants-1981_01
Patent number
US04245097

Reaction notes

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