Acetaldehyde → HCID 59510516, compound

HRID 602293Notes

Reaction equation

HRID 602293 reaction equation
[NH2:1][C:2]1[C:24]([Cl:25])=[CH:23][C:5]([C:6]([NH:8][CH2:9][CH:10]2[O:15][CH2:14][CH2:13][N:12]([CH2:16][CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH2:11]2)=[O:7])=[C:4]([O:26][CH2:27][CH3:28])[CH:3]=1.[CH:29](=O)[CH3:30].[BH4-].[Na+]>CO>[NH2:1][C:2]1[C:24]([Cl:25])=[CH:23][C:5]([C:6]([NH:8][CH2:9][CH:10]2[O:15][CH2:14][CH2:13][N:12]([CH2:16][CH:17]3[CH2:18][CH2:19][N:20]([CH2:29][CH3:30])[CH2:21][CH2:22]3)[CH2:11]2)=[O:7])=[C:4]([O:26][CH2:27][CH3:28])[CH:3]=1

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 4311764Sodium borohydrideHCID 59510469HCID 59510469, compound

Product 1

HCID 59510516HCID 59510516, compoundYield 112.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-amino-5-chloro-2-ethoxy-N-[{4-(4-piperidinylmethyl)-2-morpholinyl}-methyl]benzamide (Example 22) (1.0 g) and TEA (0.49 g) in methanol (10 ml) was added acetaldehyde (0.21 g) under ice-cooling. The mixture was stirred at the same temperature for 2 hours, and then thereto was gradually added sodium borohydride (92 mg). After completion of addition, the mixture was stirred at the same temperature for 1 hour, and warmed to room temperature to stir overnight. The reaction solution was dried under reduced pressure to be solidified, and the residue was dissolved in chloroform, washed with water, then brine, and dried over anhydrous magnesium sulfate. Then, the solvent was removed in vacuo. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1) to give the titled compound (1.2 g) as a white amorphous solid.

Workup

  1. temperaturecooling
  2. additionAfter completion of addition
  3. stirringthe mixture was stirred at the same temperature for 1 hour
  4. stirringto stir overnight
  5. customThe reaction solution was dried under reduced pressure
  6. dissolutionthe residue was dissolved in chloroform
  7. washwashed with water
  8. dry with materialbrine, and dried over anhydrous magnesium sulfate
  9. customThen, the solvent was removed in vacuo
  10. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-fbc47ec98e4c45e1a38b963b23101807
Source dataset
uspto-grants-2011_03
Patent number
US07906510B2

Reaction notes

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