1-(2-Hydroxyethyl)piperazine → 1-(3-(Di(tert-butyldimethylsiloxy)-methyl-silanyl)-propoxy)-3-(4-(2-hydroxy-ethyl)-piperidin-1-yl)-propan-2-ol

HRID 2384125Notes

Reaction equation

[N:1]1([CH2:7][CH2:8][OH:9])[CH2:6][CH2:5]N[CH2:3][CH2:2]1.[C:10]([Si:14]([CH3:34])([CH3:33])[O:15][Si:16]([CH:26]([CH2:29][CH:30]1[CH2:32][O:31]1)CC)([CH3:25])[O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])([CH3:13])([CH3:12])[CH3:11]>C(O)C>[O:15]([Si:16]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])([CH3:25])[CH2:26][CH2:29][CH2:30][O:31][CH2:32][CH:8]([OH:9])[CH2:7][N:1]1[CH2:6][CH2:5][CH:26]([CH2:29][CH2:30][OH:31])[CH2:3][CH2:2]1)[Si:14]([C:10]([CH3:11])([CH3:13])[CH3:12])([CH3:34])[CH3:33]

Participants

Conditions

Temperature: 70 °C

Procedure

2-piperazin-1-yl-ethanol (0.61 g) and ethanol (20 mL) were charged to a 100 mL RB flask equipped with a magnetic stirrer. The mixture was stirred and heated to 70° C. 1,5-Di(tert-butyl)-3-(oxiranylmethylpropyl)-1,1,3,5,5-Pentamethyltrisiloxane (2.0 g) was placed in an addition funnel and added dropwise to the flask. The mixture was stirred and maintained at 70° C. for an additional 4 hours. The reaction progress was monitored by NMR spectroscopy. Upon reaction completion, the ethanol was removed by rotovap, and the mixture was distilled under reduced pressure to remove impurities.

Workup

customequipped with a magnetic stirrer
additionadded dropwise to the flask
stirringThe mixture was stirred
temperaturemaintained at 70° C. for an additional 4 hours
customUpon reaction completion
customthe ethanol was removed by rotovap
distillationthe mixture was distilled under reduced pressure
customto remove impurities

Sources & evidence

ORD record: ord-37d81312127240a5a412271f41d6c9b4
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263669B2

Reaction notes

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