Piperidine → 1-[4-[14-(Trimethylsilyl)tetradecylamino]benzoyl)piperidine

HRID 652030

Reaction equation

HRID 652030 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl.[CH3:15][Si:16]([CH3:42])([CH3:41])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1>CN(C)C1C=CN=CC=1.CCOCC>[CH3:42][Si:16]([CH3:15])([CH3:41])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32]1[CH:33]=[CH:34][C:35]([C:36]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:37])=[CH:39][CH:40]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 201982304-[14-(Trimethylsilyl)tetradecylamino]benzoyl chloride hydrochloride

Product 1

HCID 201983121-[4-[14-(Trimethylsilyl)tetradecylamino]benzoyl)piperidine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a chilled solution of 35 ml. of piperdine, 2.5 ml. of triethylamine and 0.6 g of 4-(dimethylamino)pyridine in 100 ml. of diethyl ether is added (1/2 hour) a solution of 8.1 g. of 4-[14-(trimethylsilyl)tetradecylamino)-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 water and dried. The solvent is removed in vacuo and the solid is recrystallized 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

Sources & evidence

ORD record
ord-e66e82b2b39740f9b07787218ff6338f
Source dataset
uspto-grants-1987_06
Patent number
US04670421

Linked notes

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