Acetone → HCID 70202931, compound

HRID 617235Notes

Reaction equation

HRID 617235 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]3[NH2:19])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[BH4-].[Na+].CC(C)=O>C(O)C.[OH-].[Na+]>[ClH:1].[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C@H:13]3[CH2:18][CH2:17][CH2:16][CH2:15][C@@H:14]3[NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 240BenzaldehydeHCID 4311764Sodium borohydrideHCID 21851609HCID 21851609, compound

Product 1

HCID 70202931HCID 70202931, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

0.39 g of N-(7-chloro-quinolin-4-yl)-cyclohexane-1,2-diamine and 0.13 ml of benzaldehyde were stirred at 20° C. in 3 ml of ethanol for 3 hrs. The solvent was evaporated in order to complete the reaction. The resulting Schiff's base was again dissolved in 3 ml of ethanol, cooled in ice under argon and then treated portionwise with 0.3 g of sodium borohydride and stirred without cooling for a further 20 hrs. Excess reducing agent was decomposed by the addition of 3 ml of acetone. Thereafter, the mixture was diluted with 30 ml of 0.3N NaOH and extracted twice with 30 ml of dichloromethane each time. The crude product obtained from these extracts was purified by flash chromatography on silica gel with ethyl acetate and ethyl acetate/methanol 5:1. The purified product was converted into the hydrochloride with ethanolic hydrochloric acid and precipitated by dilution with 2-butanone. Yield: 260 mg (54%), m.p. >200° C. (dec.).

Workup

  1. customThe solvent was evaporated in order
  2. customthe reaction
  3. temperaturecooled in ice under argon
  4. temperaturewithout cooling for a further 20 hrs
  5. extractionextracted twice with 30 ml of dichloromethane each time

Sources & evidence

ORD record
ord-abaf96cfdfd14a9482477670cf715c12
Source dataset
uspto-grants-1999_09
Patent number
US05948791

Reaction notes

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