Dichloromethane → HCID 9228419, compound

HRID 427448Notes

Reaction equation

C(N(CC)CC)C.[N:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1.[N+:20]([C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1)([O-:22])=[O:21].ClCCl>CN(C=O)C>[N:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:15][CH2:16][N:17]([C:27](=[O:28])[C:26]3[CH:25]=[CH:24][C:23]([N+:20]([O-:22])=[O:21])=[CH:31][CH:30]=3)[CH2:18][CH2:19]2)=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 4 °C

Procedure

Triethylamine (3.48 ml) was added to a stirred suspension of 1-(4-pyridyl)piperazine (4.08 g) in DMF (50 ml). The mixture was cooled to 4° C., and 4-nitrobenzoylchloride (4.64 g) added. The mixture was stirred for 1 hour at 4° C. and then for 16 hours at ambient temperature. Dichloromethane (250 ml) was then added and the mixture washed with water (3×30 ml), saturated brine (1×30 ml), then dried (MgSO4) and the solvents evaporated. The residual oil was purified by flash chromatography on silica gel using 5% v/v methanol/dichloromethane and then with 10% v/v methanol/dichloromethane as eluant to give 1-(4pyridyl)-4-(4-nitrobenzoyl)piperazine (5.09 g) as a yellow solid. m.p. 158-160° C.; microanalysis. found: C, 61.3; H, 5.3; N, 17.6%; C16H16N4O3 requires: C, 61.5; H, 5.2; N, 17.9%: NMR: 3.42(6H+H2O,m), 3.87(2H,bs), 6.93(2H,d), 7.84(2H,d), 8.30(2H,d), 8.41(2H,d): MS: m/z 313 (MH)+.

Workup

waitfor 16 hours at ambient temperature
washthe mixture washed with water (3×30 ml), saturated brine (1×30 ml)
dry with materialdried (MgSO4)
customthe solvents evaporated
customThe residual oil was purified by flash chromatography on silica gel using 5% v/v methanol/dichloromethane

Sources & evidence

ORD record: ord-bf0bbd9cee944f32b521917bc2136304
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313127B1

Reaction notes

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