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

HRID 717100Notes

Reaction equation

HRID 717100 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.[Si:16](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:29]([Si:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[O:9][CH2:8][CH2:7][N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)([CH3:32])([CH3:30])[CH3:31]

Participants

6

Reactant 3

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

Product 1

HCID 453571091-(2-(tert-Butyldiphenylsilyloxy)ethyl)piperazineYield 21%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To 2-piperazin-1-yl-ethanol (2 g, 15.36 mmol) in CH2Cl2 (70 mL) and pyridine (1.85 mL, 23.04 mmol) was added DMAP (188 mg, 1.53 mmol) and TBDPS chloride (3.37 mL, 18.44 mmol) and the reaction mixture stirred at RT for 18 h. The reaction mixture was concentrated in vacuo and the crude material was purified by silica gel column chromatography, eluting with CH2Cl2 and increasing the polarity to 10% MeOH/CH2Cl2 to obtain 1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-piperazine as a colourless oil (1.1 g, 21%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude material was purified by silica gel column chromatography
  3. washeluting with CH2Cl2
  4. temperatureincreasing the polarity to 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-5b47fc25510e4416ad4c1b323f6c311f
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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