4-Hydroxybenzaldehyde → HCID 77949816, compound

HRID 643196Notes

Reaction equation

HRID 643196 reaction equation
[C:1]([CH2:3][C:4]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:5])#[N:2].[OH:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.N1CCCCC1>N1C=CC=CC=1>[OH:13][C:12](=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][NH:6][C:4](=[O:5])[C:3]([C:1]#[N:2])=[CH:20][C:19]1[CH:22]=[CH:23][C:16]([OH:15])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 8082Piperidine2×HCID 85875172HCID 85875172, compound

Product 1

HCID 77949816HCID 77949816, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

7.5 g (38 mmol 6-(cyanacetamido) hexanoic acid was dissolved in 50 ml pyridine. 4.6 g (38 mmol) 4-hydroxybenzaldehyde and 0.7 ml (7 mmol) piperidine were added to the solution and the reaction mixture was stirred for 2 hours at 50° C. A further aliquot of 0.4 ml piperidine was then added to the reaction and the solution was stirred at RT for 60 hours. The residue after evaporation of the pyridine was acidified with HCl (2N) and was extracted with ethyl acetate. The organic layer was poured into 300 ml of a saturated solution of sodium hydrogen carbonate. The aqueous layer was then carefully acidified with HCl (2N). The precipitated residue was filtered and washed with water. The dried product was crystallized from dioxane.

Workup

  1. stirringthe solution was stirred at RT for 60 hours
  2. customThe residue after evaporation of the pyridine
  3. extractionwas extracted with ethyl acetate
  4. additionThe organic layer was poured into 300 ml of a saturated solution of sodium hydrogen carbonate
  5. filtrationThe precipitated residue was filtered
  6. washwashed with water
  7. customThe dried product was crystallized from dioxane

Sources & evidence

ORD record
ord-c8138ec112ec4df4aadc4246127087e7
Source dataset
uspto-grants-2010_04
Patent number
US07700306B2

Reaction notes

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