Benzaldehyde → HCID 15718921, compound

HRID 2166139Notes

Reaction equation

HRID 2166139 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[N:16]([CH2:17][CH2:18][OH:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)[CH2:3][CH2:2]1.[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.S1C=CC=C1.[H][H]>CO.[Pd]>[C:21]1([CH2:20][N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C:8]3[N:16]([CH2:17][CH2:18][OH:19])[C:11]4=[N:12][CH:13]=[CH:14][CH:15]=[C:10]4[N:9]=3)[CH2:5][CH2:6]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 8030ThiopheneHCID 15718815HCID 15718815, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15718921HCID 15718921, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 28 parts of 2-(4-piperidinylamino)-3H-imidazo[4,5-b]pyridine-3-ethanol, 20 parts of benzaldehyde, 2 parts of a solution of thiophene in methanol 4% and 160 parts of methanol was hydrogenated at normal pressure and at room temperature with 3 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was taken up in trichloromethane and the whole was extracted with an acidic aqueous solution. The extract was washed three times with trichloromethane and treated with a sodium hydroxide solution. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was stirred in 1,1'-oxybisethane. The solid product was filtered off and dried, yielding 25.2 parts (65.1%) of 2-[[1-(phenylmethyl)-4-piperidinyl]amino]-3H-imidazo[4,5-b]pyridine-3-ethanol; mp. 125.7° C. (compound 120).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. extractionthe whole was extracted with an acidic aqueous solution
  4. washThe extract was washed three times with trichloromethane
  5. additiontreated with a sodium hydroxide solution
  6. extractionThe product was extracted with dichloromethane
  7. customThe extract was dried
  8. filtrationfiltered
  9. customevaporated
  10. filtrationThe solid product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-4fb29daafa514d418ce1337dacd909c6
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

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