Acetic Acid → HCID 68527204, compound

HRID 1932524Notes

Reaction equation

HRID 1932524 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:41]=[CH:42][C:43]=1[Cl:44])[CH2:5][NH:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][NH:21][CH2:22][C:23]([N:25]3[CH2:30][CH2:29][N:28]([CH2:31][C:32]4[CH:40]=[CH:39][C:38]5[O:37][CH2:36][O:35][C:34]=5[CH:33]=4)[CH2:27][CH2:26]3)=[O:24])=[CH:16][CH:15]=2)=[N:11][CH:12]=1.[CH:45](=O)[CH3:46].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClC(Cl)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:41]=[CH:42][C:43]=1[Cl:44])[CH2:5][N:6]([CH2:45][CH3:46])[C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:20][NH:21][CH2:22][C:23]([N:25]3[CH2:30][CH2:29][N:28]([CH2:31][C:32]4[CH:40]=[CH:39][C:38]5[O:37][CH2:36][O:35][C:34]=5[CH:33]=4)[CH2:27][CH2:26]3)=[O:24])=[CH:18][CH:19]=2)=[N:11][CH:12]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68527072HCID 68527072, compound

Product 1

HCID 68527204HCID 68527204, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

2-({4-[5-(3,4-dichlorobenzylamino)pyridin-2-yloxy]phenyl}methylamino)-1-(4-piperonylpiperazin-1-yl)ethanone (1.59 g, 2.5 mmol) was dissolved in dichloroethane (80 mL). To this solution were added acetoaldehyde (1.40 mL, 25.0 mmol) and sodium triacetyloxy borohydride (1.59 mL, 7.5 mmol) under ice cooling. To the resulting solution was added dropwise acetic acid (0.43 mL, 7.5 mmol), and this solution was stirred at room temperature for 16 hours. The resulting reaction solution was washed with a saturated sodium bicarbonate solution and brine. The organic layer was dried over anhydrous magnesium sulfate, and evaporated. The residue was then purified by silica gel column chromatography (chloroform:methanol=50:1). The obtained solid was recrystallized from ethanol, to thereby yield 0.65 g of the title compound.

Workup

  1. customThe resulting reaction solution
  2. washwas washed with a saturated sodium bicarbonate solution and brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was then purified by silica gel column chromatography (chloroform:methanol=50:1)
  6. customThe obtained solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-972db936f6b64517a49b7d3a101b71c0
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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