4-Pyridinecarboxaldehyde → HCID 20225050, compound

HRID 1249175Notes

Reaction equation

HRID 1249175 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:13]([NH2:17])[CH2:14][CH2:15][CH3:16])[CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8].[N:18]1[CH:23]=[CH:22][C:21]([CH:24]=O)=[CH:20][CH:19]=1.[BH4-].[Na+]>C(O)C>[ClH:1].[ClH:1].[N:18]1[CH:23]=[CH:22][C:21]([CH2:24][NH:17][CH:13]([C:9]2([C:4]3[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([Cl:1])[CH:3]=3)[CH2:12][CH2:11][CH2:10]2)[CH2:14][CH2:15][CH3:16])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 4311764Sodium borohydrideHCID 13083237HCID 13083237, compound

Product 1

HCID 20225050HCID 20225050, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
130 °C

Procedure

A mixture of 1-[1-(3-chloro-4-methylphenyl)cyclobutyl]butylamine (2.5 g) [see Example 10(k) of British Patent Specification No. 2098602A] and 4-pyridinecarboxaldehyde (1.5 ml) was stirred and heated at 130° C. for 18 hours. The mixture was dissolved in ethanol (50 ml) and the solution added to a solution of sodium borohydride (2.5 g) in ethanol (120 ml) and heated under reflux for 2 hours. Excess ethanol was removed by evaporation and the mixture acidified, basified and extracted into ether. Hydrogen chloride gas was passed through the dried extract to give an oil which was triturated with acetone to give N-(4-pyridylmethyl)-1-[1-(3-chloro-4-methylphenyl)cyclobutyl]butylamine dihydrochloride (m.p. 203°-206° C.).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. customExcess ethanol was removed by evaporation
  4. extractionextracted into ether
  5. extractionextract
  6. customto give an oil which
  7. customwas triturated with acetone

Sources & evidence

ORD record
ord-c42bc07904e5463e82c2b3dd552df073
Source dataset
uspto-grants-1986_12
Patent number
US04629727

Reaction notes

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