Hydroxyamine hydrochloride → 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-(2-pyrrolidon-1-yl)methylindole

HRID 1790518ノート

反応式

HRID 1790518 の反応式
[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([CH2:23][NH:24][C:25](=O)[CH3:26])[CH:21]=4)[C:16](C=O)=[CH:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.NO.[C:35]([O-])(=[O:37])[CH3:36].[Na+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([CH2:23][N:24]5[CH2:25][CH2:26][CH2:36][C:35]5=[O:37])[CH:21]=4)[CH:16]=[CH:15]3)[CH2:12][CH2:13]2)=[CH:30][CH:31]=1

参加物

5

反応物 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 220380151-[1-(4-Fluorophenethyl)piperidin-4-yl]-3-formyl-6-acetamidomethylindole

生成物 1

HCID 220379311-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-(2-pyrrolidon-1-yl)methylindole収率 89.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A liquid mixture of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-3-formyl-6-acetamidomethylindole (0.09 g) obtained in Example 370, hydroxylamine hydrochloride (0.02 g) and anhydrous sodium acetate (0.03 g) in methanol (10 ml) was stirred at room temperature for 1 hr. Then the reaction mixtures were concentrated and the residue was partitioned between ethyl acetate (20 ml) and a 1 N aqueous solution (10 ml) of sodium hydroxide. The ethyl acetate layer was washed successively with water and brine, dried over magnesium sulfate and concentrated under reduced pressure. Then the residue was crystallized from ether/hexane, collected by filtration, washed with hexane and dried to give the title compound (0.08 g) as a pale yellow powder (yield: 88.5%).

後処理

  1. customThen the reaction mixtures
  2. concentrationwere concentrated
  3. customthe residue was partitioned between ethyl acetate (20 ml)
  4. washThe ethyl acetate layer was washed successively with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThen the residue was crystallized from ether/hexane
  8. filtrationcollected by filtration
  9. washwashed with hexane
  10. customdried

出典と根拠

ORDレコード
ord-9d1a8770810041799eef5f2768e408fc
出典データセット
uspto-grants-2006_07
特許番号
US07071201B2

反応ノート

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