Chloroethane → HCID 12875760, compound

HRID 444475Notes

Reaction equation

HRID 444475 reaction equation
OC1C=C(C([C:11]([CH:13](Cl)[C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([OH:21])[CH:15]=2)=O)[Cl:10])C=CC=1O.[O:23]=[C:24]1[N:28]([CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[C:27]2[CH:35]=[CH:36][CH:37]=[CH:38][C:26]=2[NH:25]1.C(=O)([O-])[O-:40].[Na+].[Na+].CCCl>CC(CC)=O.Cl.CO.[I-].[Na+]>[ClH:10].[OH:21][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=1[OH:20])[C:13](=[O:40])[CH2:11][N:32]1[CH2:31][CH2:30][CH:29]([N:28]2[C:27]3[CH:35]=[CH:36][CH:37]=[CH:38][C:26]=3[NH:25][C:24]2=[O:23])[CH2:34][CH2:33]1

Participants

9

Reactant 4

HCID 6337ChloroethaneHCID 10340Sodium CarbonateHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 131712197HCID 131712197, compound

Product 1

HCID 12875760HCID 12875760, compoundYield 107.7%

Reagents, catalysts & solvents 4

HCID 5238Sodium IodideCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A suspension of 6.87 g of 3,4-dihydroxyphenyl chloromethylketone (trade product) and 8 g of 4-(2-oxobenzimidazolin-1-yl)piperidine (trade product), M.P. 183°-185° C., in 640 ml of methylethyl ketone, in the presence of 1.95 g of dried sodium carbonate and 0.1 g of sodium iodide, was refluxed for 12 hours. After the completion of the reaction, the precipitate was filtered off and washed with water. After drying, there were obtained 14 g of raw base which is transformed in hydrochloride in methanol by addition of hydrochloric ether. There were obtained 8 g of 1-(3,4-dihydroxy phenacyl)-4-(2-oxobenzimidazolin-1-yl)piperidine hydrochloride, white crystals melting at 310°-313° C.

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe precipitate was filtered off
  3. washwashed with water
  4. customAfter drying
  5. customthere were obtained 14 g of raw base which

Sources & evidence

ORD record
ord-e15e5995276f4fe89dd59790964cf37c
Source dataset
uspto-grants-1981_04
Patent number
US04264613

Reaction notes

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