4-Cyanobenzaldehyde → HCID 12044885, compound

HRID 1368204Notes

Reaction equation

HRID 1368204 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[C:17]([O:21][CH3:22])[C:18]=1[O:19][CH3:20])[O:6][CH2:7][C:8]([N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)=[O:9].[C:23]([C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1)#[N:24].C([BH3-])#N.[Na+]>C(O)(=O)C.CO>[CH3:22][O:21][C:17]1[CH:16]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:18]=1[O:19][CH3:20])[O:6][CH2:7][C:8]([N:10]1[CH2:11][CH2:12][N:13]([CH2:29][C:28]2[CH:31]=[CH:32][C:25]([C:23]#[N:24])=[CH:26][CH:27]=2)[CH2:14][CH2:15]1)=[O:9]

Participants

6

Reactant 3

HCID 660424-CyanobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 12044886HCID 12044886, compound

Product 1

HCID 12044885HCID 12044885, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 1-((3,4,5-trimethoxyphenoxy)methyl)carbonylpiperazine (0.22 g, 0.70 mmol) in 1% acetic acid in methanol (6 mL) was added 4-cyanobenzaldehyde (0.33 g, 2.5 mmol) and sodium cyanoborohydride (0.093 g, 1.4 mmol). The resultant mixture was stirred at ambient temperature for 1.5 hours and the mixture was then concentrated of volatiles in vacuo. Residue was taken up in ethyl acetate and washed with saturated aqueous NaHCO3 solution, water, and then brine. The organic layer was separated, dried over MgSO4, filtered and concentrated in vacuo to afford a yellow oil. Purification by flash column chromatography on silica gel afforded 0.21 g of 1-((3,4,5-trimethoxyphenoxy)methyl)carbonyl-4-(4-cyanobenzyl)piperazine, a compound of formula (Ib), as a clear oil: NMR (CDCl3) 7.6 (d, 2), 7.4 (d, 2), 6.2 (s, 2), 4.6 (s, 2), 3.8 (s, 6), 3.75 (s, 3), 3.6 (m, 4), 3.5 (s, 2), 2.2 (m, 4) ppm.

Workup

  1. concentrationthe mixture was then concentrated of volatiles in vacuo
  2. washwashed with saturated aqueous NaHCO3 solution, water
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a yellow oil
  8. customPurification by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-7a3d3f00682a4bdeada575d3ce31eb61
Source dataset
uspto-grants-2003_06
Patent number
US06573266B1

Reaction notes

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