Sodium Carbonate → 1-[2-[4-[5-Chloro-1-(4-fluorophenyl)-1H-indol-3-yl]-3,6-dihydro-1(2H)-pyridinyl]ethyl]-2-imidazolidinone

HRID 1250033Notes

Reaction equation

HRID 1250033 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[CH:6]=[C:5]2[C:18]1[CH2:19][CH2:20][NH:21][CH2:22][CH:23]=1.Cl[CH2:25][CH2:26][N:27]1[CH:31]=[CH:30][NH:29][C:28]1=[O:32].C(=O)([O-])[O-].[Na+].[Na+]>C(C(C)=O)C(C)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=1)[CH:6]=[C:5]2[C:18]1[CH2:19][CH2:20][N:21]([CH2:25][CH2:26][N:27]2[CH2:31][CH2:30][NH:29][C:28]2=[O:32])[CH2:22][CH:23]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 98838385-Chloro-1-(4-fluorophenyl)-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 183294691-(2-Chloroethyl)-1,3-dihydro-2H-imidazol-2-one

Product 1

HCID 150064421-[2-[4-[5-Chloro-1-(4-fluorophenyl)-1H-indol-3-yl]-3,6-dihydro-1(2H)-pyridinyl]ethyl]-2-imidazolidinone

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
92.5 °C

Procedure

5-chloro-1-(4-fluorophenyl)-3-(1,2,3,6-tetrahydropyridin-4-yl)indole (6.0 kg. 16.5 mol), 1-(2-chloroethyl)imidazolon (3.19 kg, 1.3 eq.), sodium carbonate (anhydrous) and methyl isobutyl ketone (60 L) were mixed. The reaction mixture was heated under N2-cover and stirring until 90-95° C., and was stirred over night at this temperature. The next day the reaction mixture was filtered while still hot. The apparatus and filter cake were washed with further 2.5 L of methyl isobutyl ketone. The combined filtrates were left over night for crystallisation. The product was isolated on a nutch, washed with 7.5 L n-Heptane and dried over night in vacuum at 60° C.

Workup

  1. temperatureThe reaction mixture was heated under N2-cover
  2. stirringwas stirred over night at this temperature
  3. filtrationThe next day the reaction mixture was filtered while still hot
  4. filtrationThe apparatus and filter cake
  5. washwere washed with further 2.5 L of methyl isobutyl ketone
  6. waitThe combined filtrates were left over night for crystallisation
  7. customThe product was isolated on a nutch
  8. washwashed with 7.5 L n-Heptane
  9. customdried over night in vacuum at 60° C.

Sources & evidence

ORD record
ord-caf61861d079497cb7d325671418698a
Source dataset
uspto-grants-2002_01
Patent number
US06335463B1

Reaction notes

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