Lithium Hydroxide → HCID 58576146, compound

HRID 511186Notes

Reaction equation

Cl.[F:2][C:3]([F:17])([F:16])[C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.C[O:19][C:20](=[O:25])[CH2:21][CH2:22][CH2:23]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[OH-].[Li+:35]>C(#N)C.O>[Li+:35].[F:17][C:3]([F:2])([F:16])[C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH2:23][CH2:22][CH2:21][C:20]([O-:25])=[O:19])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-(6-trifluoromethyl-pyridin-3-yl)-piperazine hydrochloride (440 mg; 1.65 mmol), 4-bromo-butyric acid methyl ester (322 g; 1.65 mmol), potassium carbonate (456 mg; 3.30 mmol) and potassium iodide (274 mg; 1.65 mmol) in acetonitrile (6 mL) is heated to 100° C. for 2 hours. The reaction mixture is allowed to attain room temperature, filtered and the filtrate is concentrated under high vacuum. The resulting residue is taken up in tetrahydrofuran (10 mL) and a solution of lithium hydroxide (119 mg; 4.95 mmol) in water (2 mL) is added. The resulting mixture is stirred at room temperature over night and is then diluted with acetonitrile (90 mL). The precipitate formed is then filtered and dried under high vacuum to afford the desired compound (495 mg; 1.53 mmol).

Workup

customto attain room temperature
filtrationfiltered
concentrationthe filtrate is concentrated under high vacuum
customThe precipitate formed
filtrationis then filtered
customdried under high vacuum

Sources & evidence

ORD record: ord-8bf19469fb824f079c16b59c28d38473
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096524B2

Reaction notes

Loading…