Dichloromethane → HCID 57489618, compound

HRID 1778945Notes

Reaction equation

Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].Cl.[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1)([O-:15])=[O:14].CCN(CC)CC.C(Cl)Cl>C1COCC1>[N+:13]([C:16]1[CH:17]=[CH:18][C:19]([N:22]2[CH2:27][CH2:26][N:25]([C:2]([O:4][CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[O:3])[CH2:24][CH2:23]2)=[CH:20][CH:21]=1)([O-:15])=[O:14]

Participants

Conditions

Temperature: 0 °C

Procedure

Benzyl chloroformate (0.515 mL, 3.61 mmol) was added to a mixture of 1-(4-nitrophenyl)piperazine hydrochloride (0.800 g, 3.28 mmol) and Et3N (1.14 mL, 8.21 mmol) in THF (20 mL) at 0° C. The resulting mixture was stirred at 0° C. for 1 hour then at room temperature for 2 hours. DCM (40 mL) was added and the organics were washed with saturated NaHCO3 (40 mL), water (40 mL) then dried over MgSO4. The volatiles removed in vacuo to give the title compound I3 as a yellow solid (1.11 g, 99%); 1H NMR (400 MHz, CDCl3) δ 8.04-8.01 (m, 2H), 7.32-7.18 (m, obscured), 7.15 (s, 1H), 6.72-6.69 (m, 2H), 5.06 (s, 2H), 3.62-3.54 (m, 4H), 3.37-3.26 (m, 4H).

Workup

waitat room temperature for 2 hours
washthe organics were washed with saturated NaHCO3 (40 mL), water (40 mL)
dry with materialthen dried over MgSO4
customThe volatiles removed in vacuo

Sources & evidence

ORD record: ord-79173e089ccb49e9b9850e7873d56772
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266864B2

Reaction notes

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