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

HRID 614374Notes

Reaction equation

HRID 614374 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][CH2:16][NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[OH-].[K+].[C:33](Cl)(Cl)=[O:34]>CO>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH2:15][CH2:16][N:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:33]2=[O:34])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 14797Potassium Hydroxide2×HCID 20540168N~1~-(1-Benzylpiperidin-4-yl)-N~2~-phenylethane-1,2-diamine

Product 1

HCID 155726681-(1-Benzylpiperidin-4-yl)-3-phenylimidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

200 g of 1-benzyl-4-(2-anilino-ethylamino)-piperidine and 2000 ml of toluene and 1940 ml of potassium hydroxide solution are charged into a reaction vessel. The temperature is kept between 5° and 10° C with a mixture of ice and methanol while 300 g of phosgene are introduced in the course of 3 hours. Thereafter the reaction mixture is stirred for 2 hours at room temperature. During the dropwise addition of 860 ml of potassium hydroxide, the temperature is kept below 25° C with an ice-bath. The batch is then stirred for 14 hours. The precipitated crystals are collected with suction and dried. The two-phase filtrate is separated in a separating funnel. The toluene phase is dried over 200 g of sodium sulphate, filtered and concentrated. The residue is recrystallied from 400 ml of ethanol to give the 1-(1-benzyl-4-piperidyl)-3-phenyl-imidazolidin- 2-one with a melting point of 173°-174° C.

Workup

  1. additionare introduced in the course of 3 hours
  2. customthe temperature is kept below 25° C with an ice-bath
  3. stirringThe batch is then stirred for 14 hours
  4. customThe precipitated crystals are collected with suction
  5. customdried
  6. customThe two-phase filtrate is separated in a separating funnel
  7. dry with materialThe toluene phase is dried over 200 g of sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-59bc2df252b24fa59820ae5908b8faea
Source dataset
uspto-grants-1979_03
Patent number
US04144344

Reaction notes

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