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Acetaldehyde → 1-Benzyl-4-[N-propyl-N-(3-ethylamino-2-pyridinyl)amino]piperidine

HRID 361822
ノート
印刷プレビュー

反応式

HRID 361822 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:22][CH2:23][CH3:24])[C:15]2[C:20]([NH2:21])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:25](=O)[CH3:26].C([BH3-])#N.[Na+].Cl.[OH-].[Na+]>C(O)C.C(O)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:22][CH2:23][CH3:24])[C:15]2[C:20]([NH:21][CH2:25][CH3:26])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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 177Acetaldehyde2 回HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydride2 回HCID 105680191-Benzyl-4-[N-propyl-N-(3-amino-2-pyridinyl)amino]piperidine

生成物 1

HCID 540721561-Benzyl-4-[N-propyl-N-(3-ethylamino-2-pyridinyl)amino]piperidine

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒

実験手順

A mixture of 1-benzyl-4-[N-propyl-N-(3-amino-2-pyridinyl)amino]piperidine (EXAMPLE 114, 0.35 g) in absolute ethanol (4.3 ml) under nitrogen is treated with acetaldehyde (120 μl) and sodium cyanoborohydride (84 mg) and the pH is adjusted to 5 with glacial acetic acid as measured on moistened pH test paper. The resulting mixture is stirred at 20°-25° for 48 hrs, during which additional acetaldehyde (180 μl) and sodium cyanoborohydride (70 mg) is added, and is then adjusted to pH 3 with hydrochloric acid (3M), neutralized with sodium hydroxide (5%), and concentrated under reduced pressure. The residue is chromatographed (silica gel, 70-230 mesh, 35 g; eluting with a gradient of methanol/methylene chloride (1/99-2/98)) to give the title compound, NMR (CDCl3) 7.72, 7.31, 7.27, 6.91, 6.79, 4.66, 3.51, 3.10, 2.92, 2.05, 1.74, 1.27 and 0.79δ.

後処理

  1. additionis added
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is chromatographed (silica gel, 70-230 mesh, 35 g
  4. washeluting with a gradient of methanol/methylene chloride (1/99-2/98))

出典と根拠

ORDレコード
ord-83d3acd38e8e44baa45448bb7c510357
出典データセット
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05866589

反応ノート

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