Dichloromethane → 3,5-didecoxybenzyl Amine

HRID 2055755Notes

Reaction equation

HRID 2055755 reaction equation
[CH2:1]([O:11][C:12]1[CH:13]=[C:14]([CH:19]=[C:20]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:21]=1)[CH2:15][N:16]=[N+]=[N-])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].ClCCl.[N-]=[N+]=[N-]>[Pd].CCOCC.CO>[CH2:23]([O:22][C:20]1[CH:19]=[C:14]([CH:13]=[C:12]([O:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH:21]=1)[CH2:15][NH2:16])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 33558AzideHCID 862391583,5-didecoxybenzyl Azide

Product 1

HCID 693071983,5-didecoxybenzyl AmineYield 97.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21864698Diethyl ether methanolSolvent2×

Procedure

Catalytic (5% by mass) palladium on carbon (0.51 g) was placed into a hydrogenation bottle. The bottle was then placed under N2. To the bottle, 50/50 ether methanol (10 mL) was added. 3,5-didecoxybenzyl azide (5.0 g, 11.2 mmol) was dissolved in 50/50 ether/methanol (60 mL) and transferred to the bottle. The bottle was attached to a hydrogenator with H2 pressure at 40 psi and left for 1 hour. Thin layer chromatography of the dichloromethane/10% hexanes showed the presence of an azide. The bottle was left on a hydrogenator with H2 at 40 psi for an additional hour after which time, thin layer chromatography then showed no evidence of the starting material. The contents of the bottle were then vacuum filtered over celite. The filtrate was then concentrated using rotary evaporation and then placed under high vacuum for 4 or more hours. The resulting viscous liquid was dark yellow. This produced a 4.6 g yield or a 97.9% yield of the derivative. The NMR characterization data for this derivative is as follows. 1NMR (300 MHz, CDCl3): 0.88 (t, J=6.6, 6H, CH2CH3), 1.27-1.46 (m, 28H, CH2(CH2)7), 1.77 (p, J=6.6, 4H, OCH2CH2), 3.92 (t, J=6.6, 4H, OCH2), 3.78 (s, 2H, ArCH2NH2), 6.33 (t, J=2.2, 1H, ArH), 6.44 (d, J=2.2, 2H, ArH). 13C NMR (75 MHZ, CDCl3): 14.23, 22.79, 26.16, 29.39, 29.45, 29.50, 29.69, 29.72, 32.01, 46.80, 69.04, 99.61, 105.35, 145.79, 160.58.

Workup

  1. waitThe bottle was left on a hydrogenator with H2 at 40 psi for an additional hour after which time, thin layer chromatography
  2. filtrationvacuum filtered over celite
  3. concentrationThe filtrate was then concentrated
  4. customevaporation
  5. customThis produced a 4.6 g
  6. customyield

Sources & evidence

ORD record
ord-ddfbc8fce4a747e18196017cdfad0275
Source dataset
uspto-grants-2008_02
Patent number
US07332529B2

Reaction notes

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