Water → N-(3,3-diphenylpropyl)-(1-naphthyl)ethylamine

HRID 322596

反応式

HRID 322596 の反応式
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)(=O)[CH3:18].C([BH3-])#N.[Na+].O>C(OCC)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[C:11]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][NH:10][CH2:18][CH2:17][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

参加物

7

反応物 4

HCID 962WaterHCID 136631-AcetylnaphthaleneHCID 796983,3-DiphenylpropylamineHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 70062729N-(3,3-diphenylpropyl)-(1-naphthyl)ethylamine

試薬・触媒・溶媒 2

HCID 11026Titanium isopropoxide触媒HCID 3283Diethyl Ether溶媒

実験手順

An equal molar mixture of 3,3-diphenylpropylamine (2.11 g, 10 mmol), 1′-acetonaphthone (1.70 g, 10 mmol) and 1.25 equivalents of titanium(IV) isopropoxide (3.55 g, 12.5 mmol) were stirred 4 hr at rt. The reaction mixture was then treated with a 1 M solution of ethanolic sodium cyanoborohydride (12.5 ml, 12.5 mmol) and stirred 16 hr at rt. The reaction was diluted with diethyl ether (50 ml) and treated with water (0.72 ml, 40 mmol). After mixing thoroughly the mixture was centrifuged and the ether layer decanted and concentrated to a milky oil. The oil was suspended in diethyl ether and filtered through a 0.45 μM CR PTFE Acrodisc. The diethyl ether filtrate was concentrated to afford N-(3,3-diphenylpropyl)-(1-naphthyl)ethylamine, 3U, as a clear, colorless oil; m/z (rel. int.) 365 (M+, 17), 350 (19),181 (23),155 (100), 141 (25), 115 (11), 91 (13), 77 (6).

後処理

  1. stirringstirred 16 hr at rt
  2. additionAfter mixing thoroughly the mixture
  3. customthe ether layer decanted
  4. concentrationconcentrated to a milky oil
  5. filtrationfiltered through a 0.45 μM CR PTFE Acrodisc
  6. concentrationThe diethyl ether filtrate was concentrated

出典と根拠

ORDレコード
ord-a81b2e9fe4e0436abeadacd9ae6d4090
出典データセット
uspto-grants-2001_04
特許番号
US06211244B1

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