Diethyl Ether → HCID 87678330、化合物

HRID 2421447ノート

反応式

HRID 2421447 の反応式
C[Mg+].[Br-].CCOCC.[NH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[C:15]([C:17]1[C:18]2[C:23]([CH:24]=[C:25]3[C:30]=1[CH:29]=[CH:28][CH:27]=[CH:26]3)=[CH:22][CH:21]=[CH:20][CH:19]=2)#[N:16]>C1(C)C=CC=CC=1>[CH:29]1[C:30]2[C:25](=[CH:24][C:23]3[C:18]([C:17]=2[C:15](=[NH:16])[N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:26]=[CH:27][CH:28]=1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 8082PiperidineHCID 145869-CyanoanthraceneHCID 178418689HCID 178418689、化合物

生成物 1

HCID 87678330HCID 87678330、化合物収率 62%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

A solution of MeMgBr in ether (3.3 mL, 3.0 M, 9.9 mmol) was added to a solution of piperidine (1.11 g, 13.1 mmol) in toluene (50 mL) at 50° C. The mixture was stirred for 1 h and a white precipitate formed. Next, the mixture was cooled to 0° C. and 9-cyanoantracene (2.00 g, 9.9 mmol) was added. The mixture was allowed to warm to room temperature and the mixture was stirred for 16 h subsequently. The conversion, determined by GC, appeared to be 98%. The mixture was quenched with an aqueous NH4Cl solution (1%, 150 mL). The organic phase was separated from the aqueous phase and the latter was extracted with CH2Cl2 (250 mL) twice. The combined organic phases were dried over Na2SO4, filtered and the solvents were removed under reduced pressure resulting in a sticky residue. Pure product 1.76 g (62%) was obtained by rinsing the residue with ligroin. The ligand was characterized by 1H NMR (300 MHz) (CDCl3) δ (ppm): 8.4 (s, 1H), 7.9 (m, 4H), 7.4 (m, 4H), 5.8 (bs, 1H), 4.0 (bt, 2H), 2.7 (bt, 2H), 1.8 (bm, 2H), 1.5 (p, 2H), 1.2 (bm, 2H) and by 13C-NMR (75.5 MHz) (CDCl3) δ (ppm): 163.3, 130.7, 129.4, 126.6, 125.8, 125.3, 124.6, 123.8, 123.5, 46.5, 41.8, 25.0, 23.8, 22.8.

後処理

  1. customa white precipitate formed
  2. temperatureto warm to room temperature
  3. stirringthe mixture was stirred for 16 h subsequently
  4. customThe mixture was quenched with an aqueous NH4Cl solution (1%, 150 mL)
  5. customThe organic phase was separated from the aqueous phase
  6. extractionthe latter was extracted with CH2Cl2 (250 mL) twice
  7. dry with materialThe combined organic phases were dried over Na2SO4
  8. filtrationfiltered
  9. customthe solvents were removed under reduced pressure
  10. customresulting in a sticky residue

出典と根拠

ORDレコード
ord-77eb7249996b4b92b89878ca6c6c4c59
出典データセット
uspto-grants-2011_06
特許番号
US07956140B2

反応ノート

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