Acetone → 1-Isopropyl-4-(4-nitrophenyl)piperazine

HRID 1011261Notes

Reaction equation

HRID 1011261 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].[Na].[CH3:17][C:18]([CH3:20])=O.O>ClCCCl>[CH:18]([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)([CH3:20])[CH3:17]

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 804471-(4-Nitrophenyl)piperazineHCID 5360545Sodium

Product 1

HCID 98347891-Isopropyl-4-(4-nitrophenyl)piperazine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A suspension of 1-(4-nitrophenyl)piperazine (20 g, 190 mmol, 2 eq), sodium triaectoxyborohydride (41 g, 97 mmol, 2 eq), and acetone (18.8 g, 21.3 mL, 290 mmol, 3 eq) in DCE (400 mL) is stirred in a water bath at rt for 32 h. Water (100 mL) is slowly added (gas evolution) and resulting biphasic solution is stirred for 1 h. The phases are separated and the DCE extract is washed with water (2×100 mL). The combined aqueous extracts are extracted with DCE (2×50 mL), and the combined DCE extracts are filtered through a phase separation tube. The filtrate is concentrated on a rotary evaporator and the yellow oil obtained dried under vacuum for a further 2 h. The oily product obtained solidified on standing to provide 1-isopropyl-4-(4-nitrophenyl)piperazine as a yellow solid (16.5 g, 66% recovery). The product is used in the next step without further purification. LCMS Purity: 80% by ELS detection; LCMS-ESI (m/z): calcd for C13H19N3O2 249.1; [M+H]+ found, 250.3.

Workup

  1. customresulting biphasic solution
  2. stirringis stirred for 1 h
  3. customThe phases are separated
  4. extractionthe DCE extract
  5. washis washed with water (2×100 mL)
  6. extractionThe combined aqueous extracts are extracted with DCE (2×50 mL)
  7. filtrationthe combined DCE extracts are filtered through a phase separation tube
  8. concentrationThe filtrate is concentrated on a rotary evaporator
  9. customthe yellow oil obtained
  10. customdried under vacuum for a further 2 h
  11. customThe oily product obtained

Sources & evidence

ORD record
ord-7ae2b0281b44407689b18976f3778dae
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

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