Tetrahydrofuran → 1-[2-(Trimethylsilyl)ethylcarbonyl]-4-(4-nitrophenyl)piperazine

HRID 1007125Notes

Reaction equation

HRID 1007125 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)(OC1C=CC([N+]([O-])=O)=CC=1)O[CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21].[O:35]1CCC[CH2:36]1>>[CH3:23][Si:20]([CH3:21])([CH3:22])[CH2:19][CH2:18][C:36]([N:13]1[CH2:14][CH2:15][N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:11][CH2:12]1)=[O:35]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 804471-(4-Nitrophenyl)piperazineHCID 30861164-Nitrophenyl 2-(trimethylsilyl)ethyl carbonate

Product 1

HCID 226677981-[2-(Trimethylsilyl)ethylcarbonyl]-4-(4-nitrophenyl)piperazineYield 71%

Procedure

A solution of 1-(4-nitrophenyl)piperazine (10 g, 48.31 mmol) and 2-(trimethylsilyl)ethyl p-nitrophenyl carbonate (14.4 g, 50.73 mmol) in tetrahydrofuran (220 mL) is refluxed for 3 hours with magnetic stirring and then stirred for 20 hours at room temperature. The reaction mixture is concentrated, the residue is taken up in dichloromethane and the organic phase is washed 4 times with 1N sodium hydroxide and twice with water. The organic phase is then dried over sodium sulphate, filtered and concentrated; the oily residue obtained is used without further purification in the following step (12 g, yield: 71%). 1H NMR (300 MHz, δ ppm) CDCl3: 0.04 (s, 9H), 1.02 (m, 2H), 3.43 (m, 4H), 3.65 (m, 4H), 4.22 (m, 2H), 6.82 (d, 2H), 8.13 (d, 2H).

Workup

  1. stirringstirred for 20 hours at room temperature
  2. concentrationThe reaction mixture is concentrated
  3. washthe organic phase is washed 4 times with 1N sodium hydroxide
  4. dry with materialThe organic phase is then dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe oily residue obtained
  8. customis used without further purification in the following step (12 g, yield: 71%)

Sources & evidence

ORD record
ord-6f99f1947b24468884407db31391d5b9
Source dataset
uspto-grants-2004_09
Patent number
US06794382B2

Reaction notes

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