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

HRID 2420972노트

반응식

HRID 2420972 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1d28352e3a14467fafd5fbdda0bdb7e1
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07956066B2

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