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1,1-Dichloroethane → 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-(2-pyrrolidon-1-yl)methylindole

HRID 1790510
ノート
印刷プレビュー

反応式

HRID 1790510 の反応式
[F:1][C:2]1[CH:26]=[CH:25][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](C=O)[CH:21]=4)[CH:16]=[CH:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.[CH3:28][NH2:29].C(O[BH-](O[C:40](=[O:42])[CH3:41])OC(=O)C)(=O)C.[Na+].Cl[CH:45](Cl)[CH3:46].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][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]([CH2:28][N:29]5[CH2:45][CH2:46][CH2:41][C:40]5=[O:42])[CH:21]=4)[CH:16]=[CH:15]3)[CH2:10][CH2:9]2)=[CH:25][CH:26]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 63651,1-DichloroethaneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 6364545Methylamine hydrochlorideHCID 220382961-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-formylindole

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-formylindole (400 mg) obtained in Example 130, methylamine hydrochloride (150 mg), sodium triacetoxyborohydride (480 mg), acetic acid (300 mg) and dichioroethane (10 ml) was stirred at room temperature for 2 days. Then a saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the reaction mixtures. The organic layer was separated, washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by Chromatorex NH-silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (140 mg) as an oil. This oil was crystallized from ethyl acetate by using oxalic acid (34 mg) to give the oxalate (140 mg) of the title compound as a white powder (yield: 27%).

後処理

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by Chromatorex NH-silica gel column chromatography (hexane/ethyl acetate system)

出典と根拠

ORDレコード
ord-db6f415e7e084b09b44668299b1aca5c
出典データセット
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07071201B2

反応ノート

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