Dimethylamine → 1-(4-Aminophenoxy)-3-(dimethylamino)propan-2-ol

HRID 1989004Notes

Reaction equation

[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH:10]2[CH2:12][O:11]2)=[CH:6][CH:5]=1)([O-])=O.[CH3:15][NH:16][CH3:17]>C(O)C>[NH2:1][C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH:10]([OH:11])[CH2:12][N:16]([CH3:17])[CH3:15])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-(4-nitro-phenoxymethyl)-oxirane (0.2 g, 1 mmol) in 2 mL of ethanol was added a solution of dimethylamine (2 M in methanol, 2.5 mL). The solution was stirred at 80° C. for 2 hours in a capped vial. The solvent was removed in vacuo. Hydrogenation of the residue using the procedure described in Example 1(f) gave the title compound as a brown solid. 1H NMR (300 MHz, CD3OD) δ (ppm): 6.76 (m, 2H), 6.71 (m, 2H), 4.20 (m, 1H), 3.88 (d, 2H), 3.04 (m, 2H), 2.71 (s, 6H).

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-f05bfb8d5eb94ffeb3e79a0b9b384daf
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642270B2

Reaction notes

Loading…