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

HRID 322596

Reaction equation

HRID 322596 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 3283Diethyl EtherSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a81b2e9fe4e0436abeadacd9ae6d4090
Source dataset
uspto-grants-2001_04
Patent number
US06211244B1

Linked notes

Loading…