Cyclohexanone → HCID 12891708, compound

HRID 1856565Notes

Reaction equation

HRID 1856565 reaction equation
S1C=CC=C1.[C:6]1(=O)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[C:13]1([CH2:19][N:20]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[N:22]=[C:21]2[NH:29][CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H][H]>[Pd].CO.C(O)(=O)C.C(O)C>[CH:6]1([N:33]2[CH2:34][CH2:35][CH:30]([NH:29][C:21]3[N:20]([CH2:19][C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[N:22]=3)[CH2:31][CH2:32]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

9

Reactant 4

HCID 7967CyclohexanoneHCID 8030ThiopheneHCID 30186301-(Phenylmethyl)-N-4-piperidinyl-1H-benzimidazol-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 12891708HCID 12891708, compoundYield 38.5%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To 1 part of a solution of 2 parts of thiophene in 40 parts of ethanol, are added 2 parts of cyclohexanone, 3 parts of 1-(phenylmethyl)-N-(4-piperidinyl)-1H-benzimidazol-2-amine, 1 part of acetic acid and 120 parts of methanol. The whole is hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off over Hyflo and the filtrate is evaporated. The residue is taken up in water and the whole is alkalized with sodium hydroxide. The product is extracted with tetrahydrofuran. The extract is dried, filtered and evaporated. The residue is crystallized from a mixture of 2,2'-oxybispropane and 2-propanol, yielding 1.5 parts (38.5%) of N-(1-cyclohexyl-4-piperidinyl)-1-(phenylmethyl)-1H-benzimidazol-2-amine; amine; mp. 143° C.

Workup

  1. filtrationthe catalyst is filtered off over Hyflo
  2. customthe filtrate is evaporated
  3. extractionThe product is extracted with tetrahydrofuran
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is crystallized from a mixture of 2,2'-oxybispropane and 2-propanol

Sources & evidence

ORD record
ord-7f40527dac904606af7dd3a43c643084
Source dataset
uspto-grants-1980_08
Patent number
US04219559

Reaction notes

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