Sodium Carbonate → HCID 21500297, compound

HRID 1729815Notes

Reaction equation

HRID 1729815 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:9][CH2:10][CH2:11]I)=[CH:4][CH:3]=1.[Cl:20][C:21]1[C:26]2[N:27]([CH:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[C:28](=[O:30])[NH:29][C:25]=2[CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)CC(=O)C>[Cl:20][C:21]1[C:26]2[N:27]([CH:31]3[CH2:36][CH2:35][N:34]([CH2:11][CH2:10][CH2:9][CH:8]([C:13]4[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=4)[C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[CH2:33][CH2:32]3)[C:28](=[O:30])[NH:29][C:25]=2[CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 1039681,1'-(4-Iodobutylidene)bis[4-fluorobenzene]HCID 13792107HCID 13792107, compound

Product 1

HCID 21500297HCID 21500297, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 7.4 parts of 1,1-bis(-4-fluorophenyl)-4-iodobutane, 5 parts of 7-chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one, 5 parts of sodium carbonate and 56 parts of 4-methyl-2-pentanone is stirred and refluxed overnight. After cooling, the reaction mixture is poured onto water. The organic layer is separated, dried, filtered and concentrated to half its volume. From the residue, the product is allowed to crystallize. The product is filtered off and recrystallized from a mixture of 4-methyl-2-pentanone and 2-propanol, yielding 7-chloro-1-{1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one; mp. 215.4° C.

Workup

  1. temperaturerefluxed overnight
  2. temperatureAfter cooling
  3. additionthe reaction mixture is poured onto water
  4. customThe organic layer is separated
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated to half its volume
  8. customto crystallize
  9. filtrationThe product is filtered off
  10. customrecrystallized from a mixture of 4-methyl-2-pentanone and 2-propanol

Sources & evidence

ORD record
ord-ef8e5b80d1544fa1a61b1d3824b4ea0d
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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