Potassium Carbonate → n-[8-(Naphthalen-2-ylmethyl)-8-azabicyclo[3.2.1]oct-3-yl]acetamide

HRID 29927

反応式

HRID 29927 の反応式
[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]([NH:9][C:10](=[O:12])[CH3:11])[CH2:2]2.C(N1CCC(NC2[C:36]3[C:31](=[C:32](OC)[CH:33]=[C:34](OC)[CH:35]=3)[C:30]([C:41]3[CH:46]=[CH:45]C(OC)=C[CH:42]=3)=NN=2)CC1)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].BrCC1C=CC2C(=CC=CC=2)C=1.[OH-].[Na+]>CC(C)=O>[CH:30]1[C:31]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:45]=[CH:46][C:41]=1[CH2:42][N:8]1[CH:5]2[CH2:6][CH2:7][CH:1]1[CH2:2][CH:3]([NH:9][C:10](=[O:12])[CH3:11])[CH2:4]2

参加物

7

反応物 5

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 703202-BromomethylnaphthaleneHCID 652782N-(8-Aza-bicyclo[3.2.1]oct-3-yl)-acetamideHCID 69213501N-(1-benzylpiperidin-4-yl)-5,7-dimethoxy-4-(4-methoxyphenyl)phthalazin-1-amine

生成物 1

HCID 69214902n-[8-(Naphthalen-2-ylmethyl)-8-azabicyclo[3.2.1]oct-3-yl]acetamide収率 84%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

1.6 g (9.5 mmol) of N-[8-azabicyclo[3.2.1]oct-3-yl]acetamide prepared according to Dostert et al. (European Journal of Medicinal Chemistry 1984, 19 (2), 105-110) are dissolved in 45 mL of acetone, and 5.2 g of potassium carbonate and 2.5 g (11.4 mmol) of 2-(bromomethyl)naphthalene are added. The mixture is refluxed with stirring for 18 hours. After cooling, the acetone is partially evaporated off. Water is added to the residue, and the mixture is extracted with dichloromethane. The organic phase is extracted with 1N hydrochloric acid. The acidic aqueous phase obtained is basified with 1N sodium hydroxide and then extracted with dichloromethane. The extract is washed with water and with brine, dried over anhydrous sodium sulfate and then evaporated under reduced pressure. The residue obtained is filtered on silica gel (solvent: 95/5 (v/v) dichloromethane/methanol). 2.2 g of a pasty oil are obtained (84% yield).

後処理

  1. temperatureThe mixture is refluxed
  2. temperatureAfter cooling
  3. customthe acetone is partially evaporated off
  4. additionWater is added to the residue
  5. extractionthe mixture is extracted with dichloromethane
  6. extractionThe organic phase is extracted with 1N hydrochloric acid
  7. customThe acidic aqueous phase obtained
  8. extractionextracted with dichloromethane
  9. washThe extract is washed with water and with brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. customevaporated under reduced pressure
  12. customThe residue obtained
  13. filtrationis filtered on silica gel (solvent: 95/5 (v/v) dichloromethane/methanol)

出典と根拠

ORDレコード
ord-1f91637baf4f4351af4521a0e5eabbb3
出典データセット
uspto-grants-2008_09
特許番号
US07423030B2

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