Ethanol → HCID 20278959, compound

HRID 1156332Notes

Reaction equation

HRID 1156332 reaction equation
C(O)C.[F:4][C:5]1[CH:33]=[CH:32][C:8]([C:9]([CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:31])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N+:28]([O-])=O)[CH2:13][CH2:12]2)=[O:10])=[CH:7][CH:6]=1.[H][H]>[Pt].CO>[NH2:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:21]([NH:20][CH2:19][CH2:18][CH2:17][N:14]1[CH2:15][CH2:16][CH:11]([C:9](=[O:10])[C:8]2[CH:7]=[CH:6][C:5]([F:4])=[CH:33][CH:32]=2)[CH2:12][CH2:13]1)=[O:31]

Participants

6

Reactant 3

HCID 702EthanolHCID 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 thophene 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. The mother liquor is evaporated, yielding a second fraction of 6 parts (36%) of 2-amino-N-[3-[4-(4-fluorobenzoyl)-1-piperidinyl]propyl]benzamide as an oily residue.

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-260783f976f44b07ab9727507c523e3c
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

Loading…