2-(Dimethylamino)ethanol → 3-[2-(Dimethylamino)ethoxy]aniline

HRID 964633Notes

Reaction equation

HRID 964633 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.N(C(OCC)=O)=NC(OCC)=O.[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24]O>C1COCC1>[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][O:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[NH2:1]

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 115683-AminophenolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 167782053-[2-(Dimethylamino)ethoxy]aniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure described in part E of Example 1 (R), (S)-α-[[2-[((1,1-dimethylethyl)dimethylsilyl)oxy]-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl]amino]-4-methoxybenzeneacetic acid was condensed with 3-[2-(dimethylamino)ethoxy]aniline to generate the title compound. The 3-[2-(dimethylamino)ethoxy]aniline was prepared by treating commercial 3-aminophenol with diethyl azo dicarboxylate, φ3P, and 2-(dimethylamino)ethanol in THF.

Sources & evidence

ORD record
ord-71deefbadbb24b94ad1b3f5e5e6ec001
Source dataset
uspto-grants-1998_06
Patent number
US05770615

Reaction notes

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