2-Chloroquinoline → 1-[(4-fluorophenyl)methyl]-N-[1-[2-(2-quinolinyloxy)ethyl]-4-piperidinyl]1H-benzimidazol-2-amine

HRID 637422Notes

Reaction equation

HRID 637422 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][OH:27])[CH2:21][CH2:20]2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]=1>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][O:27][C:31]3[CH:40]=[CH:39][C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[N:32]=3)[CH2:21][CH2:20]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 119282-ChloroquinolineHCID 24758Sodium hydrideHCID 128916994-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino]-1-piperidineethanol

Product 1

HCID 135881151-[(4-fluorophenyl)methyl]-N-[1-[2-(2-quinolinyloxy)ethyl]-4-piperidinyl]1H-benzimidazol-2-amineYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.5 Parts of 4-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino]-1-piperidineethanol and 135 parts of N,N-dimethylformamide were stirred at room temperature and 0.75 parts of a sodium hydride dispersion 50% were added. After stirring for one hour at room temperature, 2.5 parts of 2-chloroquinoline were added and the whole was stirred overnight at room temperature. The reaction mixture was poured onto water and the product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was crystallized from acetonitrile, yielding 4.3 parts (58%) of 1-[(4-fluorophenyl)methyl]-N-[1-[2-(2-quinolinyloxy)ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 149.9° C. (compound 77)

Workup

  1. stirringthe whole was stirred overnight at room temperature
  2. additionThe reaction mixture was poured onto water
  3. extractionthe product was extracted with 4-methyl-2-pentanone
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-4d74ca1cce00497591855460afa13961
Source dataset
uspto-grants-1985_12
Patent number
US04556660

Reaction notes

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