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

HRID 322596

반응식

HRID 322596 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매HCID 3283Diethyl Ether용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a81b2e9fe4e0436abeadacd9ae6d4090
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211244B1

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