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

HRID 1516360Notes

Reaction equation

HRID 1516360 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) d 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-992b1cf4cb9b4f4cb9f01837c0a8de20
Source dataset
uspto-grants-2012_07
Patent number
US08227474B2

Reaction notes

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