N,N,N',N',N'',N''-Hexamethylmethanetriamine → 2-Di-n-propylamino-8-(1-oxo-3-(dimethylamino)-prop-2-enyl)-1,2,3,4-tetrahydronaphthalene

HRID 22138

Reaction equation

HRID 22138 reaction equation
[CH2:1]([N:4]([CH2:18][CH2:19][CH3:20])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([C:15](=[O:17])[CH3:16])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].[CH3:21][N:22]([CH:24](N(C)C)N(C)C)[CH3:23]>C1(C)C=CC=CC=1>[CH2:18]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([C:15](=[O:17])[CH:16]=[CH:21][N:22]([CH3:24])[CH3:23])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 79831N,N,N',N',N'',N''-Hexamethylmethanetriamine2×HCID 1322768-Acetyl-2-(dipropylamino)tetralin

Product 1

HCID 543506572-Di-n-propylamino-8-(1-oxo-3-(dimethylamino)-prop-2-enyl)-1,2,3,4-tetrahydronaphthaleneYield 107.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-di-n-propylamino-8-acetyl-1,2,3,4-tetrahydronaphthalene (0.3 g, 1.1 mmol), prepared as in Example 5, and tris(dimethylamino)methane (0.32 g, 2.2 mmol) in toluene was heated to reflux for 5 hours and at 60° for 18 hours. An additional aliquot of tris(dimethylamino)methane (0.16 g, 1.1. mmol) was added and the reaction stirred at 60° for an additional 2 hours. The reaction was concentrated to give 2-di-n-propylamino-8-(1-oxo-3-(dimethylamino)-prop-2-enyl)-1,2,3,4-tetrahydronaphthalene (0.39 g) as a viscous, orange oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 hours and at 60° for 18 hours
  3. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-d7ffdd075c76443bad0f87b97ad3b524
Source dataset
uspto-grants-1995_06
Patent number
US05426226

Linked notes

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