Iodoethane → 1-Ethyl-4-(4-iodophenyl)piperazine

HRID 447327Notes

Reaction equation

HRID 447327 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:21][CH3:22]>CC(C)=O>[CH2:21]([N:11]1[CH2:12][CH2:13][N:8]([C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=2)[CH2:9][CH2:10]1)[CH3:22]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 41478451-(4-Iodophenyl)piperazine

Product 1

HCID 137206691-Ethyl-4-(4-iodophenyl)piperazineYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred mixture of 1-(4-iodophenyl)piperazine (5.76 g, 20 mmol) and K2CO3 (5.44 g, 40 mmol) in acetone (200 mL) was added iodoethane (2.58 mL, 32 mmol) dropwise over 1 min. After addition, the resulting mixture was stirred at rt for 21 h. The resulting precipitate was filtered off and rinsed with EtOAc (2×60 mL). The filtrate was concentrated to dryness to give a whiteish yellow solid. Trituration with MeOH (10 mL) and H2O (250 mL), followed by suction filtration (rinsed with H2O) gave the title compound as a yellow solid (5.37 g, 85%) after drying. 1H NMR (400 MHz, DMSO-d6) δ 7.46 (d, J=7.6 Hz, 2H), 6.76 (d, J=8.0 Hz, 2H), 3.13-3.07 (m, 4H), 2.48-2.43 (m, 4H), 2.34 (q, J=7.2 Hz, 2H), 1.01 (t, J=7.2 Hz, 3H); MS ESI 317.0 [M+H]+, calcd. for [C12H17IN2+H]+ 317.0.

Workup

  1. additionAfter addition
  2. filtrationThe resulting precipitate was filtered off
  3. washrinsed with EtOAc (2×60 mL)
  4. concentrationThe filtrate was concentrated to dryness
  5. customto give a whiteish yellow solid
  6. filtrationTrituration with MeOH (10 mL) and H2O (250 mL), followed by suction filtration (rinsed with H2O)

Sources & evidence

ORD record
ord-22be027bdc894b6682d3dc40d243d4ad
Source dataset
uspto-grants-2013_07
Patent number
US08481533B2

Reaction notes

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