Ethanol → 1-Carbazol-9-yl-3-[(furan-2-ylmethyl)-amino]-propan-2-ol

HRID 1776168Notes

Reaction equation

[O:1]1[CH2:3][CH:2]1[CH2:4][N:5]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2.[CH2:18]([NH2:24])[C:19]1[O:23][CH:22]=[CH:21][CH:20]=1.C(O)C>CO>[CH:16]1[C:17]2[N:5]([CH2:4][CH:2]([OH:1])[CH2:3][NH:24][CH2:18][C:19]3[O:23][CH:22]=[CH:21][CH:20]=3)[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]=2[CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A suspension of 9-(oxiran-2-ylmethyl)-9H-carbazole (2.97 g, 13.3 mmol) in a solution of furfurylamine (5.3 mL, 60 mmol) and ethanol (11 mL) was heated to 110° C. for 15 minutes in a Biotage Initiator microwave reactor. The resulting solution was diluted with methanol and cooled in an ice bath to precipitate a white solid. The solid was recrystallized by dissolving in a minimal volume of hot methanol and slowly cooled to give the desired product as a fine crystalline white solid (2.4 g, 57%). 1H NMR (CDCl3, 300 MHz) δ 8.10-8.08 (d, 2H, J=8.1 Hz), 7.46-7.44 (m, 3H), 7.32-7.25 (m, 4H), 6.29-6.27 (dd, 1H, J=1.8, 3.3 Hz), 6.11-6.10 (d, 1H, J=3 Hz), 4.39-4.38 (d, 1H, J=2.1 Hz), 4.37 (d, 1H, J=0.9 Hz), 4.21-4.17 (m, 1H), 3.75 (s, 2H), 2.85-2.79 (dd, 1H, J=3.8, 12.3 Hz), 2.69-2.62 (dd, 1H, J=8.4, 12.3 Hz), 2.00 (br s, 2H). ESI m/z: 321.1 (M+H). HPLC analysis: (C18, 10-90% acetonitrile in water+0.1% trifluoroacetic acid over 10 min: retention time, % area at 254 nm): 6.1 min, 99.0%.

Workup

temperaturecooled in an ice bath
customto precipitate a white solid
customThe solid was recrystallized
dissolutionby dissolving in a minimal volume of hot methanol
temperatureslowly cooled

Sources & evidence

ORD record: ord-1139834084f24f698323f9e3b1dce91e
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265772B2

Reaction notes

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