N-{4-[4-(2-Hydroxyethyloxy)phenyl]butyl}phthalimide → HCID 11537093, compound

HRID 457238Notes

Reaction equation

HRID 457238 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][N:15]2C(=O)C3=CC=CC=C3C2=O)=[CH:7][CH:6]=1>CN.CO>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][NH2:15])=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 22566183N-{4-[4-(2-Hydroxyethyloxy)phenyl]butyl}phthalimide

Product 1

HCID 11537093HCID 11537093, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6329MethylamineSolvent

Procedure

The crude protected amine 114 (1.2 g, 35 mmol) was dissolved in 40 mL of a 2 N solution of methyl amine in dry methanol and the reaction mixture was stirred overnight at room temperature. After this time the solvent was removed under reduced pressure and the residue was purified by flash chromatography (silica gel, 5:1:0.1 chloroform/methanol/concentrated ammonium hydroxide) to give free amine 115 (0.25 g, 35%) as a clear oil. 1H NMR (300 MHz, DMSO-d6) δ 1.58 (m, 4H), 2.55 (m, 2H), 2.73 (m, 2H), 3.83 (m, 2H), 3.97 (m, 2H), 6.83 (d, 2H), 7.07 (d, 2H), 7.82 (s, 1H).

Workup

  1. customAfter this time the solvent was removed under reduced pressure
  2. customthe residue was purified by flash chromatography (silica gel, 5:1:0.1 chloroform/methanol/concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-e17cd101376943fc84d1bba61afd0e84
Source dataset
uspto-grants-2007_03
Patent number
US07186833B2

Reaction notes

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