Potassium Carbonate → 1-[(4-fluorophenyl)methyl]-N-[1-[2-(2-pyrimidinylthio)ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine

HRID 637424Notes

Reaction equation

HRID 637424 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[SH:7].Cl.Cl.Cl[CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][CH:16]([NH:19][C:20]2[N:24]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[C:23]3[CH:33]=[CH:34][CH:35]=[CH:36][C:22]=3[N:21]=2)[CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)C>[F:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][N:24]2[C:23]3[CH:33]=[CH:34][CH:35]=[CH:36][C:22]=3[N:21]=[C:20]2[NH:19][CH:16]2[CH2:15][CH2:14][N:13]([CH2:12][CH2:11][S:7][C:2]3[N:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH2:18][CH2:17]2)=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12891728N-[1-(2-chloroethyl)-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine dihydrochlorideHCID 178418793HCID 178418793, compound

Product 1

HCID 135880911-[(4-fluorophenyl)methyl]-N-[1-[2-(2-pyrimidinylthio)ethyl]-4-piperidinyl]-1H-benzimidazol-2-amineYield 35.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.12 parts of 2-pyrimidinethiol, 4.6 parts of N-[1-(2-chloroethyl)-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine dihydrochloride, 4 parts of potassium carbonate and 80 parts of 2-propanone was stirred for 3 days at room temperature. The reaction mixture was filtered and the filtrate was evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2-propanone and 2,2'oxybispropane, yielding 1.7 parts (35.8%) of 1-[(4-fluorophenyl)methyl]-N-[1-[2-(2-pyrimidinylthio)ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 146.1°-147.7° C. (compound 91).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. customThe residue was crystallized from a mixture of 2-propanone and 2,2'oxybispropane

Sources & evidence

ORD record
ord-700fa3c3ee1a453ca082227ca7bc7e24
Source dataset
uspto-grants-1985_12
Patent number
US04556660

Reaction notes

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