4-[4-(1,4,7-Trioxaoct-1-yl)phenyl]-N-benzyloxycarbonylbutylamine → 4-[4-(1,4,7-Trioxaoct-1-yl)phenyl]butylamine

HRID 25138Notes

Reaction equation

HRID 25138 reaction equation
[O:1]([C:9]1[CH:14]=[CH:13][C:12]([CH:15](C(OCC2C=CC=CC=2)=O)[CH2:16][CH2:17][CH2:18][NH2:19])=[CH:11][CH:10]=1)[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH3:8]>C(O)C.[Pd]>[O:1]([C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])=[CH:13][CH:14]=1)[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH3:8]

Participants

4

Reactant 1

HCID 673669224-[4-(1,4,7-Trioxaoct-1-yl)phenyl]-N-benzyloxycarbonylbutylamine

Product 1

HCID 225661364-[4-(1,4,7-Trioxaoct-1-yl)phenyl]butylamineYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Compound 106 (800 mg, 2.0 mmol) in ethanol (20 mL), was subjected to 1 atmosphere of H2 in the presence of 10% Palladium on carbon (100 mg, cat.) with stirring for 5 h. After standing overnight, the reaction was purged with N2 then suction filtered through celite and washed off the celite with methylene chloride. The solvents were evaporated and chromatographed (silica gel, 200:10:1 methylene chloride/methanol/concentrated ammonium hydroxide) to afford 530 mg (>99%) of amine 107. 1H NMR (300 MHz, CDCl3) δ 1.31 (br s, 2H), 1.41-1.52 (m, 2H), 1.55-1.67 (m, 2H), 2.56 (t, J=7.7 Hz, 2H), 2.70 (t, J=7.0 Hz, 2H), 3.39 (s, 3H), 3.58 (m, 2H), 3.72 (m, 2H), 3.84 (t, J=4.9 Hz, 2H), 4.12 (t, J=5.3 Hz, 2H), 6.83 (d, J=8.7 Hz, 2H), 7.07 (d, J=8.7 Hz, 2H). CI MS m/z=268 [C15H25NO3+H]+.

Workup

  1. waitAfter standing overnight
  2. customthe reaction was purged with N2
  3. filtrationthen suction filtered through celite
  4. washwashed off the celite with methylene chloride
  5. customThe solvents were evaporated
  6. customchromatographed (silica gel, 200:10:1 methylene chloride/methanol/concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-4f4b3a54cc1f45b58b440e6867ddc9cc
Source dataset
uspto-grants-2005_02
Patent number
US06858615B2

Reaction notes

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