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

HRID 2420972ノート

反応式

HRID 2420972 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1d28352e3a14467fafd5fbdda0bdb7e1
出典データセット
uspto-grants-2011_06
特許番号
US07956066B2

反応ノート

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