Potassium Carbonate → HCID 9820840, compound

HRID 1057594Notes

Reaction equation

[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:21])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH2:29]([N:31]([CH2:34][CH2:35]Cl)[CH2:32][CH3:33])[CH3:30]>CN(C=O)C>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:30][CH2:29][N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 9-benzyl-9H-Carbazol-4-ol (0.0305 g, 0.1116 mmol), potassium carbonate (0.0308 g, 0.2232 mmol), and DMF (1.0 mL) is stirred at 100° C. Diethylaminoethyl chloride hydrochloride (0.0230 g, 0.1339 mmol) is added in aliquots over 40 min. After 2.3 h, an additional 0.032 g of potassium carbonate and 0.023 g of diethylaminoethyl chloride hydrochloride are added. The mixture is stirred overnight and then the solvent is removed and the residue partitioned between CH2Cl2 and aq. sodium bicarbonate. The organic layers are dried over sodium sulfate. Chromatography on silica gel (15 mL) using acetone-hexane (20/80) gave 0.0382 g of the title compound as a solid; mp 79-80.5° C.; IR (drift) 2965, 1581, 1457, 1439, 1356, 1342, 1333, 1268, 1147, 1112, 1053, 782, 750, 729, 713 cm−1; 1H NMR (CDCl3) δ1.14, 2.75, 3.13, 4.36, 5.50, 6.71, 6.98, 7.12, 7.2-7.4, 8.38. Anal. Calcd for C25H28N2O: C, 80.61; H, 7.58; N, 7.52. Found: C, 79.90; H, 7.52; N, 7.43.

Workup

stirringThe mixture is stirred overnight
customthe solvent is removed
customthe residue partitioned between CH2Cl2 and aq. sodium bicarbonate
dry with materialThe organic layers are dried over sodium sulfate

Sources & evidence

ORD record: ord-863f28e1e7c0410dbfc5a76db0386175
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06514968B1

Reaction notes

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