Water → HCID 21830850, compound

HRID 2393430Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH2:19][CH3:20])CC)C.C([CH:23]([C:27](Cl)=[O:28])[C:24](Cl)=[O:25])C.[OH2:30]>ClCCl.C(OCC)C>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:27](=[O:28])[CH2:23][C:24]([O:25][CH2:19][CH3:20])=[O:30])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a cooled (-20° C.) and stirred solution of N-benzylpiperazine (10 g, 56.7 mmol) and triethylamine (8.7 ml, 62.4 mmol) in dichloromethane (200 ml) was added ethyl malonyl chloride (8.5 ml, 66.4 mmol) over 10 minutes, under nitrogen. The mixture was allowed to warm to room temperature and it was stirred for 1 hour before water (100 ml) and diethyl ether (500 ml) were added. The organic phase was decanted off, washed with water (1×70 ml), 10% aqueous sodium bicarbonate (1×75 ml), brine (1×75 ml), then dried (MgSO4) and concentrated. Flash chromatography of the residue (silica gel, ethyl acetate--ethanol, 95:5) afforded 9.53 g, (58%) of the title compound as a colourless oil. δ (360 MHz, CDCl3), 1.28 (3H, t, J=7.2Hz), 2.48 (4H, br s), 3.45 (2H, s) 3.47 (2H, br s), 3.56 (2H, br s), 3.68 (2H, br s), 4.19 (2H, q, J=7.2Hz), 7.24-7.36 (5H, m); m/e (ES) 291 (M+1)+.

Workup

temperatureto warm to room temperature
additionwere added
customThe organic phase was decanted off
washwashed with water (1×70 ml), 10% aqueous sodium bicarbonate (1×75 ml), brine (1×75 ml)
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-9f525cdd5bac4aeeb95c023eb26063bc
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05807857

Reaction notes

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