Formaldehyde → 1-(2-Hydroxyethyl)-4-methylpiperazine

Temperature

50 °C

In THF (30 ml) were added N-(2-hydroxyethyl)piperazine (500 mg, 3.84 mmol), a solution of formaldehyde (3117 mg, 38.41 mmol) and sodium cyanoborohydride (1207 mg, 19.20 mmol). The mixture was heated up to 50° C. overnight under stirring. After cooling some water was added and the mixture was extracted with DCM (3×). The organic layers were dried over MgSO4 and evaporated. The residue was purified over a silica plug with DCM/MeOH 9:1 as eluant to afford an oil (370 mg, Y=67%). 1H NMR (DMSO-d6) δ 4.45 (t, J=5.3 Hz, 1H), 3.51-3.45 (m, 2H), 3.02-2.84 (m, 4H), 2.71-2.64 (m, 2H), 2.61 (s, 3H), 2.58-2.53 (m, 2H), 2.47-2.43 (m, 2H).

1. additionwas added
2. extractionthe mixture was extracted with DCM (3×)
3. dry with materialThe organic layers were dried over MgSO4
4. customevaporated
5. customThe residue was purified over a silica plug with DCM/MeOH 9:1 as eluant
6. customto afford an oil (370 mg, Y=67%)

ORD record

ord-fb44b903ea3d44e8a26aab9d8bf059fa

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07838522B2