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

HRID 2384125
Notes
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Reaction equation

HRID 2384125 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 866322801,5-Di(tert-butyl)-3-(oxiranylmethylpropyl)-1,1,3,5,5-Pentamethyltrisiloxane

Product 1

HCID 668726811-(3-(Di(tert-butyldimethylsiloxy)-methyl-silanyl)-propoxy)-3-(4-(2-hydroxy-ethyl)-piperidin-1-yl)-propan-2-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. customequipped with a magnetic stirrer
  2. additionadded dropwise to the flask
  3. stirringThe mixture was stirred
  4. temperaturemaintained at 70° C. for an additional 4 hours
  5. customUpon reaction completion
  6. customthe ethanol was removed by rotovap
  7. distillationthe mixture was distilled under reduced pressure
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes