Ethanol → HCID 20278959, compound

HRID 1248219Notes

Reaction equation

HRID 1248219 reaction equation
S1C=CC=C1.C(O)C.[F:9][C:10]1[CH:38]=[CH:37][C:13]([C:14]([CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:36])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N+:33]([O-])=O)[CH2:18][CH2:17]2)=[O:15])=[CH:12][CH:11]=1.[H][H]>[Pt].CO>[NH2:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:26]([NH:25][CH2:24][CH2:23][CH2:22][N:19]1[CH2:20][CH2:21][CH:16]([C:14](=[O:15])[C:13]2[CH:12]=[CH:11][C:10]([F:9])=[CH:38][CH:37]=2)[CH2:17][CH2:18]1)=[O:36]

Participants

7

Reactant 4

HCID 702EthanolHCID 8030ThiopheneHCID 20278956HCID 20278956, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20278959HCID 20278959, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

To 1 part of a solution of 2 parts of thiophene in 40 parts of ethanol are added 18 parts of N-[3-[4-(4-fluorobenzoyl)-1-piperidinyl]propyl]-2-nitrobenzamide and 200 parts of methanol. The whole is hydrogenated at normal pressure and at room temperature with 2 parts of platinum-on-charcoal catalyst 5%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The oily residue is crystallized from 2-propanol. The product is filtered off and dried, yielding 7.5 parts (45%) of 2-amino-N-[3-[4-(4-fluorobenzoyl)-1-piperidinyl]propyl]benzamide; mp. 113.2° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. customThe oily residue is purified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  5. customThe pure fractions are collected
  6. customthe eluent is evaporated
  7. customThe oily residue is crystallized from 2-propanol
  8. filtrationThe product is filtered off
  9. customdried

Sources & evidence

ORD record
ord-a2dc9131f34e4e6daada914b3fca26f2
Source dataset
uspto-grants-1985_06
Patent number
US04522945

Reaction notes

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