Piperidine → 3-Fluoro-4-(hexadecylamino)benzoylpiperidine

HRID 1156122Notes

Reaction equation

HRID 1156122 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.[F:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[NH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[C:28](Cl)=[O:29]>CCOCC>[F:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[NH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[C:28]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:29]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 205364403-Fluoro-4-hexadecylaminobenzoyl chloride hydrochloride

Product 1

HCID 541786193-Fluoro-4-(hexadecylamino)benzoylpiperidine

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 3-fluoro-4-hexadecylaminobenzoyl 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 diethyl ether to yield 3-fluoro-4-(hexadecylamino)benzoylpiperidine.

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 diethyl ether

Sources & evidence

ORD record
ord-38ce32555697411a8339b8ca0d93a0bd
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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