Potassium Carbonate → N,N-Diethyl-4-[(8-azabicyclo[3.2.1]oct-3-ylidene)phenylmethyl]benzamide Hydrochloride

HRID 1267503

反応式

HRID 1267503 の反応式
[CH2:1]([N:3]([CH2:28][CH3:29])[C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[C:18]2[CH2:24][CH:23]3[N:25](C)[CH:20]([CH2:21][CH2:22]3)[CH2:19]2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].[Cl:36]C(OCC(Cl)(Cl)Cl)=O>[Zn].C1C=CC=CC=1>[ClH:36].[CH2:28]([N:3]([CH2:1][CH3:2])[C:4](=[O:27])[C:5]1[CH:6]=[CH:7][C:8]([C:11](=[C:18]2[CH2:24][CH:23]3[NH:25][CH:20]([CH2:21][CH2:22]3)[CH2:19]2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:9][CH:10]=1)[CH3:29]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 870632,2,2-Trichloroethyl chloroformateHCID 9952263N,N-diethyl-4-[(8-methyl-8-azabicyclo[3.2.1]oct-3-ylidene)phenylmethyl]benzamide

生成物 1

HCID 18545680N,N-Diethyl-4-[(8-azabicyclo[3.2.1]oct-3-ylidene)phenylmethyl]benzamide Hydrochloride

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 241Benzene溶媒

実験手順

A 100 mL benzene suspension of 3.1 g (5.6 mmol) N,N-diethyl-4-[(8-methyl-8-azabicyclo[3.2.1]oct-3-ylidene)phenylmethyl]benzamide, 3.45 g (25 mmol) K2CO3, and 1.5 mL (10 mmol) 2,2,2-trichloroethyl chloroformate was allowed to reflux for 2 h. The reaction was cooled, filtered, and the solvent evaporated. The residual oil was dissolved in MeOH then stirred at reflux with 2.6 g (40 mmol) zinc powder for 1 h. After cooling, the reaction was filtered through celite and partitioned between 3N NaOH and CH2Cl2. The organic layer was washed with brine, dried over K2CO3, filtered, and concentrated (2.1 g, 5.6 mmol). The resulting clear oil was dissolved in Et2O, filtered, and the product precipitated after the addition of ethereal HCl; mp 128-132° C. MS m/z (MH+) 375. 1H NMR 300 MHz (DMSO-d6) δ 7.15-7.4 (m, 9H), 3.9-4.0 (m, 2H), 3.15-3.3 (m, 2H), 2.55-2.65 (m, 2H), 2.25-2.35 (m, 4H), 1.9-2.0 (m, 2H), 1.75-1.85 (m, 2H), 1.0-1.2 (m, 6H). Anal calc C25H30N2O.HCl (3% H2O): C, 70.89; H, 7.71; N, 6.61. Found: C, 70.52; H, 7.41; N, 6.24.

後処理

  1. temperatureto reflux for 2 h
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. customthe solvent evaporated
  5. dissolutionThe residual oil was dissolved in MeOH
  6. temperatureAfter cooling
  7. filtrationthe reaction was filtered through celite
  8. custompartitioned between 3N NaOH and CH2Cl2
  9. washThe organic layer was washed with brine
  10. dry with materialdried over K2CO3
  11. filtrationfiltered
  12. concentrationconcentrated (2.1 g, 5.6 mmol)
  13. dissolutionThe resulting clear oil was dissolved in Et2O
  14. filtrationfiltered
  15. customthe product precipitated
  16. additionafter the addition of ethereal HCl

出典と根拠

ORDレコード
ord-cff11921d3cc40f99a6e17f26982e00d
出典データセット
uspto-grants-2003_04
特許番号
US06552036B2

関連ノート

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