EDTA disodium salt → Terbinafine

HRID 1175202

反応式

HRID 1175202 の反応式
Cl/[CH:2]=[CH:3]/[CH2:4][N:5]([CH3:17])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.C(N([CH2:34][C:35]([O-])=O)CC(O)=O)CN(CC([O-])=O)CC(O)=O.[Na+].[Na+]>Cl[Ni]Cl.C1COCC1>[CH3:6][C:7]([C:34]#[C:35]/[CH:2]=[CH:3]/[CH2:4][N:5]([CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=12)[CH3:17])([CH3:16])[CH3:8]

参加物

5

反応物 2

HCID 8759EDTA disodium saltHCID 9834733(E)-3-Chloro-N-methyl-N-(1-naphthylmethyl)-2-propen-1-amine

生成物 1

HCID 1549008Terbinafine

試薬・触媒・溶媒 2

HCID 24385Nickel Dichloride触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

The mixture is cooled to 50° C. and 15.5 g (0.0572 mol) crude N-(trans-3-chloro-2-propenyl)-N-methyl-1-naphthalene-methylamine, 20 ml THF and 74 mg NiCl2 (0.77 molar percent) introduced. The reaction mixture is heated at 90°-95° C. for 1 hour, cooled to 20°/25° C. and 130 ml of a 2.5% (w/v) aqueous solution of EDTA disodium salt added, the phases are separated and the aqueous phase re-extracted with 70 ml chilled toluene. The combined organic phases are washed with 2×90 ml water and concentrated to a residue, thus giving 18.2 g (greater than theoretical yield) terbinafine with a purity of 83.6% (HPLC A %).

後処理

  1. temperatureThe reaction mixture is heated at 90°-95° C. for 1 hour
  2. additionadded
  3. customthe phases are separated
  4. extractionthe aqueous phase re-extracted with 70 ml
  5. temperaturechilled toluene
  6. washThe combined organic phases are washed with 2×90 ml water
  7. concentrationconcentrated to a residue

出典と根拠

ORDレコード
ord-f4bb78528cd24f21ac9fcd3b7ec3fc94
出典データセット
uspto-grants-2010_11
特許番号
US07838704B2

関連ノート

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