Potassium Iodide → HCID 20360368, compound

HRID 2082677Notes

Reaction equation

HRID 2082677 reaction equation
Cl.Cl[CH2:3][CH2:4][NH:5][CH:6]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.[Cl:21][C:22]1[CH:37]=[CH:36][C:25]2[N:26]([CH:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[C:27](=[O:29])[NH:28][C:24]=2[CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[F:13][C:10]1[CH:11]=[CH:12][C:7]([CH:6]([NH:5][CH2:4][CH2:3][N:33]2[CH2:32][CH2:31][CH:30]([N:26]3[C:25]4[CH:36]=[CH:37][C:22]([Cl:21])=[CH:23][C:24]=4[NH:28][C:27]3=[O:29])[CH2:35][CH2:34]2)[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 1046075-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 3017749N-[Bis(4-fluorophenyl)methyl]-2-chloroethan-1-amine--hydrogen chloride (1/1)

Product 1

HCID 20360368HCID 20360368, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 10 parts of N-(2-chloroethyl)-4-fluoro-α-(4-fluorophenyl)benzenemethanamine hydrochloride, 7.3 parts of 5-chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one, 10.6 parts of sodium carbonate, 0.1 parts of potassium iodide and 80 parts of 4-methyl-2-pentanone is stirred and refluxed overnight. Water is added to the reaction mixture. The precipitated product is filtered off and set aside. From the filtrate, the organic phase is separated, washed with water, dried, filtered and evaporated. The residue is stirred in 4-methyl-2-pentanone. The solid product is filtered off, combined with the precipitated product, obtained above, and crystallized from 4-methyl-2-pentanone. The product is filtered off and dried in vacuo at 95° C, yielding 5 parts of 1-{1-[2-{[bis(4-fluorophenyl)methyl]amino}ethyl]-4-piperidinyl}-5-chloro-1,3-dihydro-2H-benzimidazol-2-one; mp. 198.6° C.

Workup

  1. temperaturerefluxed overnight
  2. filtrationThe precipitated product is filtered off
  3. customFrom the filtrate, the organic phase is separated
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. stirringThe residue is stirred in 4-methyl-2-pentanone
  9. filtrationThe solid product is filtered off
  10. customobtained above, and
  11. customcrystallized from 4-methyl-2-pentanone
  12. filtrationThe product is filtered off
  13. customdried in vacuo at 95° C

Sources & evidence

ORD record
ord-d7bf29c4a1b442038f67a63a33954eef
Source dataset
uspto-grants-1978_04
Patent number
US04082755

Reaction notes

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