Phosgene → 1-(1-Benzylpiperidin-4-yl)-3-phenylimidazolidin-2-one

HRID 614371Notes

Reaction equation

HRID 614371 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH2:5]([N:12]1[CH2:17][CH2:16][CH:15]([NH:18][CH2:19][CH2:20][NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1(C)C=CC=CC=1.[OH-].[K+]>[CH2:5]([N:12]1[CH2:13][CH2:14][CH:15]([N:18]2[CH2:19][CH2:20][N:21]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:1]2=[O:2])[CH2:16][CH2:17]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 20540168N~1~-(1-Benzylpiperidin-4-yl)-N~2~-phenylethane-1,2-diamine

Product 1

HCID 155726681-(1-Benzylpiperidin-4-yl)-3-phenylimidazolidin-2-oneYield 66.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 14797Potassium HydroxideSolvent2×

Procedure

With stirring, 15 g of phosgene are introduced at 5° to 10° C in the course of 1 hour into a suspension of 10 g of 1-benzyl-4-(2-phenylamino-1-ethylamino)-piperidine in 100 ml of toluene and 48.5 ml of 3N potassium hydroxide solution. After stirring for 2 hours at 5° to 10° C, the reaction mixture is made alkaline with 43 ml of 6N potassium hydroxide solution and brought to room temperature. After it has been stirred for a further 15 hours at room temperature, the reaction mixture is filtered with suction and the residue is recrystallised from isopropanol-methanol to yield 7.2 g of 1-(1-benzyl-4-piperidinyl)-3-phenyl-2-imidazolidinone.

Workup

  1. stirringAfter stirring for 2 hours at 5° to 10° C
  2. custombrought to room temperature
  3. stirringAfter it has been stirred for a further 15 hours at room temperature
  4. filtrationthe reaction mixture is filtered with suction
  5. customthe residue is recrystallised from isopropanol-methanol

Sources & evidence

ORD record
ord-73b45104871d4af5acea485a79c12950
Source dataset
uspto-grants-1979_03
Patent number
US04144344

Reaction notes

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