Benzaldehyde → HCID 11516025, compound

HRID 601593Notes

Reaction equation

HRID 601593 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:20]=[CH:19][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:18])[CH3:17])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CO>[CH2:21]([NH:1][CH2:2][CH2:3][C:4]1[CH:20]=[CH:19][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:18])[CH3:17])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 59717864HCID 59717864, compound

Product 1

HCID 11516025HCID 11516025, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine N-{4-[4-(2-amino-ethyl)-phenoxy]-phenyl}-acetamide (100 mg, 0.37 mmol), benzaldehyde (47 mg, 0.44 mmol), 3 Å molecular sieves (300 mg), and methanol (3 mL) and stir overnight at room temperature. Filter off the sieves then add sodium borohydride (28 mg) to the reaction and stirred at room temperature for 2 hours. Concentrate on a rotary evaporator and purified by radial chromatography on silica gel eluting with 10% conc. ammonium hydroxide in ethanol and chloroform to yield N-{4-[4-(2-benzylamino-ethyl)-phenoxy]-phenyl}-acetamide, (61 mg): 1H NMR (CDCl3, 300.00 MHz): 7.51-6.88 (m, 13H), 3.84 (s, 2H), 2.97-2.78 (m, 4H), 2.21 (s, 3H), 1.55 (s, 1H); HPLC=99% (5/95 to 95/5 ACN/(0.1% TFA in water) over 10 minutes, Zorbax SB-Phenyl 4.6 mm×15 cm×5 micron, λ=254 nM.

Workup

  1. filtrationFilter off the sieves
  2. customadd sodium borohydride (28 mg) to the reaction
  3. concentrationConcentrate on a rotary evaporator
  4. custompurified by radial chromatography on silica gel eluting with 10% conc. ammonium hydroxide in ethanol and chloroform

Sources & evidence

ORD record
ord-5236f37cd89f419696a3f790cfb079bd
Source dataset
uspto-grants-2011_03
Patent number
US07902372B2

Reaction notes

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