Potassium Iodide → 1-(4-fluorophenylmethyl)-N-{1-[2-(4-morpholinyl)ethyl]-4-piperidinyl}-1H-benzimidazol-2-amine trihydrochloride

HRID 1856574Notes

Reaction equation

HRID 1856574 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[ClH:7].Cl.[Cl:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]2[N:23]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:22]3[CH:32]=[CH:33][CH:34]=[CH:35][C:21]=3[N:20]=2)[CH2:14][CH2:13]1.[I-].[K+]>CN(C)C=O>[ClH:9].[ClH:7].[ClH:9].[F:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:23]2[C:22]3[CH:32]=[CH:33][CH:34]=[CH:35][C:21]=3[N:20]=[C:19]2[NH:18][CH:15]2[CH2:14][CH2:13][N:12]([CH2:11][CH2:10][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[CH2:17][CH2:16]2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8083MorpholineHCID 12891728N-[1-(2-chloroethyl)-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine dihydrochloride

Product 1

HCID 233451531-(4-fluorophenylmethyl)-N-{1-[2-(4-morpholinyl)ethyl]-4-piperidinyl}-1H-benzimidazol-2-amine trihydrochlorideYield 18.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3.6 parts of morpholine, 4.8 parts of N-[1-(2-chloroethyl)-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine dihydrochloride, 0.1 parts of potassium iodide and 135 parts of N,N-dimethylformamide is stirred and heated overnight at 70° C. The reaction mixture is poured onto water and the product is extracted with methylbenzene. The extract is dried, filtered and evaporated. The residue is converted into the hydrochloride salt in methanol. The salt is filtered off and dried, yielding 1 part (18.3%) of 1-(4-fluorophenylmethyl)-N-{1-[2-(4-morpholinyl)ethyl]-4-piperidinyl}-1H-benzimidazol-2-amine trihydrochloride; mp.+300° C.

Workup

  1. additionThe reaction mixture is poured onto water
  2. extractionthe product is extracted with methylbenzene
  3. customThe extract is dried
  4. filtrationfiltered
  5. customevaporated
  6. filtrationThe salt is filtered off
  7. customdried

Sources & evidence

ORD record
ord-eb56b0dfcc404ad98adaa01d9e22b8f9
Source dataset
uspto-grants-1980_08
Patent number
US04219559

Reaction notes

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