Sodium Carbonate → 1-(2-ethoxyethyl)-2-[hexahydro-4-(4-chlorobenzhydryl)-1H-1,4-diazepin-1-yl]-1H-benzimidazole

HRID 2229807Notes

Reaction equation

HRID 2229807 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[N:15]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[CH3:2].Cl[CH:23]([C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.CCN(CC)CC>[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[N:15]1[CH2:21][CH2:20][CH2:19][N:18]([CH:23]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)[CH2:17][CH2:16]1)[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2415844-Chlorobenzhydryl chlorideHCID 9984168Emedastine EP Impurity E

Product 1

HCID 98701361-(2-ethoxyethyl)-2-[hexahydro-4-(4-chlorobenzhydryl)-1H-1,4-diazepin-1-yl]-1H-benzimidazole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of compound 15 (2 mmols) and 21 (2 mmols) in methylene chloride (10 mL) and Et3N (0.3 mL) is stirred under an inert atmosphere. The solution is warmed and the course of the reaction is followed by TLC. When the reaction is complete, dil. aq. Na2CO3 is added to the solution, shaken, and the layers are separated. The aqueous layer is extracted with additional CH2Cl2, the combined organic extracts are washed with half-saturated brine, dried (Na2SO4), filtered and concentrated under reduced pressure giving the crude product. The desired compound 1-(2-ethoxyethyl)-2-[hexahydro-4-(4-chlorobenzhydryl)-1H-1,4-diazepin-1-yl]-1H-benzimidazole 25 is obtained by purification of the crude product with the use of HPLC.

Workup

  1. temperatureThe solution is warmed
  2. customthe layers are separated
  3. extractionThe aqueous layer is extracted with additional CH2Cl2
  4. washthe combined organic extracts are washed with half-saturated brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customgiving the crude product

Sources & evidence

ORD record
ord-48433f2970a44511ab3e57213c42b647
Source dataset
uspto-grants-2002_07
Patent number
US06420560B1

Reaction notes

Loading…