Potassium Carbonate → Benzamide

HRID 1267506

反応式

HRID 1267506 の反応式
C([N:3](CC)[C:4](=[O:19])[C:5]1[CH:10]=[CH:9][C:8](C(=O)C2C=CC=CC=2)=[CH:7][CH:6]=1)C.C(N1C2CCC1CC(=O)C2)CC1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.[Zn].Cl[Ti](Cl)(Cl)Cl>[C:4]([NH2:3])(=[O:19])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 7559904-benzoyl-N,N-diethylbenzamideHCID 134285068-(2-Phenylethyl)-8-azabicyclo[3.2.1]octan-3-one

生成物 1

HCID 2331Benzamide

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 24193Titanium Tetrachloride触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A suspension of 52 g (0.8 mole) of zinc powder and 800 mL of THF was cooled in an ice bath 44 mL (0.4 mole) of TiCl4 was added dropwise with stirring. The ice bath was removed and the reaction refluxed for 2 h. A solution of 26.45 g (0.094 mole) of N,N-diethyl-4-benzoylbenzamide and 23.9 g (0.094 mole) of 8-phenethyl-8-azabicyclo[3.2.1]octan-3-one, in 100 mL of THF was added dropwise and the reaction was refluxed 4 h. After cooling, the reaction mixture was poured into a beaker containing excess K2CO3 and ice. The mixture was extracted with ether, washed with brine, dried (K2CO3) and concentrated. There was obtained 47 g (˜0.1 mol) of crude (±)-N,N-diethyl-4-[(8-phenethyl-8-azabicyclo[3:2:1]oct-3-ylidene)phenylmethyl]benzamide as an oil. A sample of the oil and 38.33 g (0.1 mole) of (+)-ditoluoyl-D-tartaric acid were combined in 600 mL of acetonitrile. The solid was collected and recrystallized twice from acetonitrile. The solid was collected and partitioned between dilute sodium hydroxide and CH2Cl2. The organic solution was dried (K2CO3) and concentrated. The residue was converted to a hydrochloride salt (Et2O/HCl). It was recrystallized from 2-PrOH to give 5.6 g of white solid. Et2O, filtered, and precipitated after the addition of ethereal HCl; mp 210-211° C. MS m/z (MH+) 479. 1H NMR 300 MHz (CDCl3) δ 12.6 (s, 1H), 7.2-7.45 (m, 14H), 3.85 (S, 2H), 3.5-3.1 (m, 10H), 2.6 (d, 1H), 2.5 (d, 2H), 2.05 (m, 2H), 1.2 (br. s, 3H), 1.1 (br. s, 3H). [α]D25=−3.7°.

後処理

  1. additionwas added dropwise
  2. customThe ice bath was removed
  3. temperaturethe reaction refluxed for 2 h
  4. temperaturethe reaction was refluxed 4 h
  5. temperatureAfter cooling
  6. additionthe reaction mixture was poured into a beaker
  7. extractionThe mixture was extracted with ether
  8. washwashed with brine
  9. dry with materialdried (K2CO3)
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-01332cb29f3a4f189bfcc9f71a578a41
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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