Phenylacetaldehyde → 2-Phenyl-N-(2-phenylethyl)ethan-1-amine

HRID 222497

反応式

HRID 222497 の反応式
[C:1]1([CH2:7][CH:8]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]1([CH2:16][CH2:17][NH2:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH2:8]([NH:18][CH2:17][CH2:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 998PhenylacetaldehydeHCID 1001PhenethylamineHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 227912-Phenyl-N-(2-phenylethyl)ethan-1-amine収率 11%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of phenylacetaldehyde (6.0 g, 50 mmol) and 2-phenylethylamine in THF (200 mL) is added sodium triacetoxy-borohydride drop wise. The solution is stirred under nitrogen overnight at room temperature. The solution is quenched with aq. saturated sodium bicarbonate (200 mL), and extracted with EtOAc (4×100 mL). The organic extracts are combined, dried and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; EtOAc/MeOH 9:1) to provide 1.25 g (11%) of the compound D as a clear oil. M+H+=226.10.

後処理

  1. customThe solution is quenched with aq. saturated sodium bicarbonate (200 mL)
  2. extractionextracted with EtOAc (4×100 mL)
  3. customdried
  4. concentrationconcentrated under vacuum
  5. customThe residue is purified by flash chromatography (silica gel; EtOAc/MeOH 9:1)

出典と根拠

ORDレコード
ord-cff4338f9c0b418ea107075245d3082a
出典データセット
uspto-grants-2012_06
特許番号
US08207183B2

関連ノート

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