Benzaldehyde → HCID 70619511, compound

HRID 2083274Notes

Reaction equation

HRID 2083274 reaction equation
[C:1]([O:5][C:6]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][NH:14][C:15]2[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=2[C:17]([NH2:19])=[O:18])[CH2:8][CH2:7]1)(=[O:4])[CH2:2][CH3:3].[CH:30](=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.N1CCCCC1.[OH:44][S:45]([OH:48])(=[O:47])=[O:46]>C(O)C.O>[OH2:4].[OH2:37].[S:45]([OH:48])([OH:47])(=[O:46])=[O:44].[C:1]([O:5][C:6]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][N:14]2[C:15]3[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:17](=[O:18])[NH:19][CH:30]2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:8][CH2:7]1)(=[O:4])[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 1118Sulfuric AcidHCID 8082PiperidineHCID 30501702-({2-[4-Phenyl-4-(propanoyloxy)piperidin-1-yl]ethyl}amino)benzene-1-carboximidic acid

Product 1

HCID 70619511HCID 70619511, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 2-[2-(4-propionoxy-4-phenylpiperidino)ethylamino]benzamide (12.55 g), benzaldehyde (3.55 g), piperidine (1.35 g), and absolute ethanol (80 ml) was refluxed for 30 hrs. The solvent was removed on a rotovap. The thick oily product was chromatographed using silica gel and 5% isopropanol in chloroform. The product was isolated and dissolved in 30 ml 95% ethanol The solution was made acid with 4N H2SO4 and then 90 ml H2O was added. After 1 hr, the product was isolated and recrystallized from 850 ml 95% ethanol; yield 8.7 g, m.p. 186°-189° (d).

Workup

  1. temperaturewas refluxed for 30 hrs
  2. customThe solvent was removed on a rotovap
  3. customThe thick oily product was chromatographed
  4. customThe product was isolated
  5. customthe product was isolated
  6. customrecrystallized from 850 ml 95% ethanol

Sources & evidence

ORD record
ord-04c6ff51afa4428f949433ffa37e1351
Source dataset
uspto-grants-1978_04
Patent number
US04085107

Reaction notes

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