Pyridine → 1-(2-(tert-Butyldiphenylsilyloxy)ethyl)piperazine

HRID 1771169Notes

Reaction equation

HRID 1771169 reaction equation
[N:1]1([CH2:7][CH2:8][OH:9])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[C:16]([Si:20](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:19])([CH3:18])[CH3:17]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Si:20]([O:9][CH2:8][CH2:7][N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 76771-(2-Hydroxyethyl)piperazineHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 453571091-(2-(tert-Butyldiphenylsilyloxy)ethyl)piperazineYield 96.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-(Piperazin-1-yl)ethanol (1.000 g, 7.68 mmol) was dissolved in DCM (35.1 ml) and pyridine (0.932 ml, 11.52 mmol) followed by DMAP (0.094 g, 0.77 mmol) were added. tert-butylchlorodiphenylsilane (2.368 ml, 9.22 mmol) was added to the solution and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the concentrate was purified by column chromatography (ISCO, eluting with 10% MeOH/DCM) to give the title product (2.73 g, yield: 96%).

Workup

  1. additionwere added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe concentrate was purified by column chromatography (ISCO, eluting with 10% MeOH/DCM)

Sources & evidence

ORD record
ord-ec8224cbfee444f7a0bf22a42c95b63d
Source dataset
uspto-grants-2016_02
Patent number
US09248140B2

Reaction notes

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