Water → HCID 56785630, compound

HRID 2200362Notes

Reaction equation

[CH3:1][CH:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][CH2:24][C:25]#[N:26].O>CN(C)C=O>[C:25]([CH2:24][CH2:23][CH2:22][N:7]1[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:3][CH:2]1[CH3:1])#[N:26]

Participants

Conditions

Temperature: 25 °C

Procedure

To the stirred solution of tert-butyl 3-methylpiperazine-1-carboxylate (prepared according to procedure reported in US200876758A1, 2008, 5 g, 24.97 mmol) in N,N-dimethylformamide (50 ml) were added potassium carbonate (17.25 g, 125 mmol) and 4-bromobutanenitrile (2.98 ml, 30.0 mmol) at 25° C. The resulting solution was stirred at 25° C. for 16 h. The progress of the reaction was monitored by TLC. After completion of the reaction water (100 ml) was added and extracted with dichloromethane (3×60 ml). The combined extract was washed with brine (25 ml) and dried over sodium sulphate, filtered and concentrated to give crude compound. The crude compound was purified by column chromatography over silica gel (100-200) using 15% ethyl acetate in hexane to obtain the title compound (5 g, 75%).

Workup

additionwas added
extractionextracted with dichloromethane (3×60 ml)
extractionThe combined extract
washwas washed with brine (25 ml)
dry with materialdried over sodium sulphate
filtrationfiltered
concentrationconcentrated
customto give crude compound
customThe crude compound was purified by column chromatography over silica gel (100-200)

Sources & evidence

ORD record: ord-7b208adbed704a808b3aa8372bc88b98
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359367B2

Reaction notes

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