Lithium Hydroxide → HCID 58576078, compound

HRID 511198Notes

Reaction equation

Cl.[C:2]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].C[O:20][C:21](=[O:26])[CH2:22][CH2:23][CH2:24]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[OH-].[Li+:36]>C(#N)C.O>[Li+:36].[C:2]([C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH2:18][CH2:17][CH2:16][N:15]([CH2:24][CH2:23][CH2:22][C:21]([O-:26])=[O:20])[CH2:14][CH2:13]2)=[CH:10][CH:11]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-(4-tert-butyl-phenyl)-[1,4]diazepane hydrochloride (220 mg; 0.82 mmol, prepared in accordance with Example 161), 4-bromo-butyric acid methyl ester (160 mg; 0.82 mmol), potassium carbonate (113 mg; 0.82 mmol) and potassium iodide (136 mg; 0.82 mmol) in acetonitrile (5 mL) is heated to 100° C. for 3 hours. The reaction mixture is allowed to attain room temperature and filtered. The filtrate is diluted with a solution of lithium hydroxide (59 mg; 2.46 mmol) in water (2 mL) and the resulting mixture is stirred at room temperature over night. All volatiles are then removed under high vacuum and more lithium hydroxide solution is added to drive the reaction to completion. Acetonitrile is added and the precipitate formed is then filtered and dried under high vacuum to afford the desired product (514 mg) which is used in the next step without further purification.

Workup

customto attain room temperature
filtrationfiltered
customAll volatiles are then removed under high vacuum and more lithium hydroxide solution
additionis added
customthe reaction to completion
customthe precipitate formed
filtrationis then filtered
customdried under high vacuum

Sources & evidence

ORD record: ord-7f2403647d1c44c7950dc6c8bde5fbe8
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096524B2

Reaction notes

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