Potassium Carbonate → 2-Chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]benzaldehyde

HRID 2420972Notes

Reaction equation

HRID 2420972 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Cl:8][C:9]1[CH:16]=[C:15]([O:17][CH2:18][CH2:19][CH2:20]Cl)[CH:14]=[CH:13][C:10]=1[CH:11]=[O:12].C([O-])([O-])=O.[K+].[K+]>C(O)CCC.O>[Cl:8][C:9]1[CH:16]=[C:15]([O:17][CH2:18][CH2:19][CH2:20][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH:14]=[CH:13][C:10]=1[CH:11]=[O:12]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 574347552-Chloro-4-(3-chloro-propoxy)-benzaldehyde

Product 1

HCID 575254242-Chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]benzaldehydeYield 63.6%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

N-Methylpiperazine (2.16 g, 21.5 mmol), 2-chloro-4-(3-chloro-propoxy)-benzaldehyde (3.19 g, 10.8 mmol), K2CO3 (4.46 g, 32.3 mmol), and KI (1.02 g, 5.38 mmol) were stirred in n-butanol (22 mL) at 90° C. for 18 h. The reaction mixture was diluted with water and then extracted three times with EtOAc. The combined extracts were dried (Na2SO4), filtered, and concentrated, yielding the crude product, which was purified by Method 1 to afford 2.04 g (63%) of an orange oil. 1H NMR (400 MHz, CD3OD): 10.3 (s, 1H), 7.86 (d, J=8.0, 1H), 7.08 (d, J=2.0, 1H), 7.00 (dd, J=8.0, 2.0, 1H), 4.15 (t, J=8.0, 2H), 3.00-2.30 (br s, 10H), 2.29 (s, 3H), 2.05-1.90 (m, 2H).

Workup

  1. extractionextracted three times with EtOAc
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customyielding the crude product, which
  6. customwas purified by Method 1

Sources & evidence

ORD record
ord-1d28352e3a14467fafd5fbdda0bdb7e1
Source dataset
uspto-grants-2011_06
Patent number
US07956066B2

Reaction notes

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