Dichloromethane → N-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-1-(trifluoroacetyl)piperidin-4-amine

HRID 39673

反応式

HRID 39673 の反応式
ClCCl.Cl.[F:5][C:6]([F:17])([F:16])[C:7]([N:9]1[CH2:14][CH2:13][CH:12]([NH2:15])[CH2:11][CH2:10]1)=[O:8].[O:18]1[C:23]2[CH:24]=[CH:25][C:26]([CH:28]=O)=[CH:27][C:22]=2[O:21][CH2:20][CH2:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[O:18]1[C:23]2[CH:24]=[CH:25][C:26]([CH2:28][NH:15][CH:12]3[CH2:13][CH2:14][N:9]([C:7](=[O:8])[C:6]([F:5])([F:16])[F:17])[CH2:10][CH2:11]3)=[CH:27][C:22]=2[O:21][CH2:20][CH2:19]1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 866331901-(4-Aminopiperidin-1-YL)-2,2,2-trifluoroethan-1-one hydrochloride

生成物 1

HCID 57815185N-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-1-(trifluoroacetyl)piperidin-4-amine

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To 20 mL of a dichloromethane suspension containing 1.0 g of 1-(trifluoroacetyl)piperidine-4-amine hydrochloride, 0.71 g of 2,3-dihydro-1,4-benzodioxin-6-carbaldehyde and 0.25 mL of acetic acid were added, the mixture was stirred at room temperature for 2 hours. The reaction mixture was added with 1.37 g of sodium triacetoxyborohydride was added and stirred at the same temperature for 30 minutes. The solvent was removed under reduced pressure, then water and ethyl acetate were added thereto, and the reaction mixture was adjusted to pH 1.5 with 1 mol/L hydrochloric acid. The aqueous layer was separated and washed with ethyl acetate, then ethyl acetate was added thereto, and the resultant solution was adjusted to pH 7.8 with an aqueous saturated sodium hydrogen carbonate solution. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, and the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 1.4 g of a colorless oily substance, N-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-1-(trifluoroacetyl)piperidine-4-amine.

後処理

  1. additionwere added
  2. additionwas added
  3. stirringstirred at the same temperature for 30 minutes
  4. customThe solvent was removed under reduced pressure
  5. additionwater and ethyl acetate were added
  6. customThe aqueous layer was separated
  7. washwashed with ethyl acetate
  8. additionethyl acetate was added
  9. customThe organic layer was separated
  10. extractionthe aqueous layer was extracted with ethyl acetate
  11. washthe resultant solution was washed with an aqueous saturated sodium chloride solution
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-ea7f4eea487243e5bfaa01ff26bd8467
出典データセット
uspto-grants-2013_09
特許番号
US08524738B2

関連ノート

読み込み中…