Diisopropylethylamine → HCID 59135785, compound

HRID 1972722Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH:10]([CH2:14][OH:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:17](Cl)([O:19]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(C(C)C)CC)(C)C>ClCCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]2[C:17](=[O:19])[O:15][CH2:14][CH:10]2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of (4-benzyl-piperazin-2-yl)methanol (250 mg, 1.21 mmol) in anhydrous DCE (8.0 mL) was added triphosgene (133 mg, 0.45 mmol, 0.37 eq) followed by diisopropylethylamine (0.25 mL, 1.45 mmol, 1.2 eq). The mixture was stirred at 50° C. under N2 for 16 h. The mixture was cooled to rt, quenched with aqueous, saturated NH4Cl solution (2.0 mL), and poured into EtOAc. The organic phase was washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by MPLC (Biotage®, gradient elution 80 to 100% EtOAc/hexane) to give the product (91.2 mg, 32%) as a clear oil, 1H-NMR (300 MHz, CD3OD) 7.35 to 7.24 (m, 5H), 4.38 (t, 1H), 3.96 to 3.87 (m, 2H), 3.71 to 3.66 (m, 1H), 3.57 (q, 2H), 3.14 to 3.07 (m, 1H), 2.97 to 2.93 (m, 2H), 2.04 (dt, 1H), 1.93 (t, 1H); ES-MS m/z 233.2 [M+H]+, RT (min) 0.29.

Workup

temperatureThe mixture was cooled to rt
customquenched with aqueous, saturated NH4Cl solution (2.0 mL)
additionpoured into EtOAc
washThe organic phase was washed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by MPLC (Biotage®, gradient elution 80 to 100% EtOAc/hexane)

Sources & evidence

ORD record: ord-31edfc4491ba4cb1a9f06f8d890aaca0
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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