Propanal → HCID 23353482, compound

HRID 235148Notes

Reaction equation

HRID 235148 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[C:16]3[N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[CH:27](=O)[CH2:28][CH3:29].C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[C:16]3[N:19]3[CH2:24][CH2:23][N:22]([CH2:27][CH2:28][CH3:29])[CH2:21][CH2:20]3)=[CH:11][CH:10]=2)=[O:7])=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 527PropanalHCID 5003444Sodium cyanoborohydrideHCID 23353520HCID 23353520, compound

Product 1

HCID 23353482HCID 23353482, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 7-(4-chlorobenzamido)-1-(1-piperazinyl)-naphthalene (0.20 g, 0.547 mmol, the product of Example 12), propionaldehyde (0.041 mL, 0.563 mmol) and sodium cyanoborohydride (0.103 g, 1.64 mmol)in methanol (12 mL) and acetic acid (1.2 mL) was stirred at ambient temperature for 20 hours. The solvent was removed at reduced pressure and the residue was partitioned between methylene chloride and saturated aqueous sodium bicarbonate. Phases were separated and the organic layer was washed with brine, dried, concentrated onto silica gel and flash chromatographed (1×3 inches). Elution proceeded as follows: ethyl acetate (50 mL) unweighed forrun; ethyl acetate (250 mL) 0.164 g of yellow foam. The foam was triturated with pentane and 0.079 g (28%) of the title compound was collected as a white solid. mp 130°-132° C. Analysis calculated for C24H26ClN3O: C, 70.66; H, 6.42; N, 10.30. Found: C, 70.91; H, 6.66; N, 10.50.

Workup

  1. customThe solvent was removed at reduced pressure
  2. customthe residue was partitioned between methylene chloride and saturated aqueous sodium bicarbonate
  3. customPhases were separated
  4. washthe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated onto silica gel and flash
  7. customchromatographed (1×3 inches)
  8. washElution
  9. customThe foam was triturated with pentane and 0.079 g (28%) of the title compound
  10. customwas collected as a white solid

Sources & evidence

ORD record
ord-fe036cbe31c14adfa37f0c4e0c643897
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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