Triethylamine → 2-(4-(4-Nitrophenyl)piperazin-1-yl)ethanol

HRID 456862Notes

Reaction equation

HRID 456862 reaction equation
Br[CH2:2][CH2:3][OH:4].[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)([O-:7])=[O:6].C([O-])([O-])=O.[K+].[K+].CCN(CC)CC>C(Cl)Cl.O>[N+:5]([C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]([CH2:2][CH2:3][OH:4])[CH2:16][CH2:15]2)=[CH:12][CH:13]=1)([O-:7])=[O:6]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 804471-(4-Nitrophenyl)piperazine

Product 1

HCID 27639362-(4-(4-Nitrophenyl)piperazin-1-yl)ethanolYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

7.5 g (60 mmol) of 2-bromoethanol is added, under argon atmosphere, to a mixture of 10.35 g (50 mmol) of 1-(4-nitrophenyl)piperazine, 7.6 g (55 mmol) of K2CO3 and 9 ml (65 mmol) of Et3N in 200 ml of CH2Cl2. The whole is then heated at 45° C. for 18 hours. The reaction mixture is finally diluted with 50 ml water, agitated and decanted. The organic phase is washed with 50 ml of salt water, dried over MgSO4, filtered and concentrated under vacuum. The residue is crystallized from diisopropyl ether. A yellow solid is obtained with a yield of 89%. Melting point: 98–99° C.

Workup

  1. customdecanted
  2. washThe organic phase is washed with 50 ml of salt water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue is crystallized from diisopropyl ether
  7. customA yellow solid is obtained with a yield of 89%

Sources & evidence

ORD record
ord-47fb220006ef4657a08a2b8cee1e8a13
Source dataset
uspto-grants-2007_03
Patent number
US07186752B2

Reaction notes

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