Water → [2-(6-Fluoro-chroman-8-yloxy)-ethyl]-[3-(5-fluoro-1H-indol-3-yl)-propyl]-amine

HRID 1954244Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH2:13][CH2:14]Cl)[CH:11]=1)[O:8][CH2:7][CH2:6][CH2:5]2.[F:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[C:20]2[CH2:26][CH2:27][CH2:28][NH2:29].C(N(CC)CC)C.O>CS(C)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH2:13][CH2:14][NH:29][CH2:28][CH2:27][CH2:26][C:20]3[C:19]4[C:23](=[CH:24][CH:25]=[C:17]([F:16])[CH:18]=4)[NH:22][CH:21]=3)[CH:11]=1)[O:8][CH2:7][CH2:6][CH2:5]2

Participants

Conditions

Temperature: 90 °C

Procedure

A solution 2-(6-fluorochroman-8-yloxy)ethylchloride (0.25 g, 7.1 mmol), 3-(5-fluoro-1H-indol-3-yl)-propylamine (0.42 g, 2.2 mmol) and triethylamine (0.22 g, 2.2 mmol) in anhydrous dimethylsulfoxide (20 ml) was allowed to stir for 14 hours at 90° C. The mixture was poured into water (100 ml) and extracted with methylene chloride (3×100 ml). The organic layer was washed with water (3×150 ml), dried over anhydrous sodium sulfate, filtered and the solvent was removed under vacuum. Chromatography (10% methanol-methylene chloride plus ammonium hydroxide) afforded 0.25 g (60%) as a white solid: mp 137-138.5° C.

Workup

extractionextracted with methylene chloride (3×100 ml)
washThe organic layer was washed with water (3×150 ml)
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customthe solvent was removed under vacuum
customChromatography (10% methanol-methylene chloride plus ammonium hydroxide) afforded 0.25 g (60%) as a white solid

Sources & evidence

ORD record: ord-52ac3ec3befd43099378dfe7fc076d69
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06121307

Reaction notes

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