Dimethylamine → 1-(6-(Dimethylamino)-2-naphthalenyl)-1-dodecanone

HRID 1788340Notes

Reaction equation

HRID 1788340 reaction equation
[CH3:1][N:2](P(N(C)C)(N(C)C)=O)[CH3:3].CNC.CO[C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:27](=[O:39])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH:23]=2)[CH:18]=1>C1C=CC=CC=1>[CH3:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][C:27]([C:22]1[CH:21]=[CH:20][C:19]2[CH:18]=[C:17]([N:2]([CH3:3])[CH3:1])[CH:26]=[CH:25][C:24]=2[CH:23]=1)=[O:39]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 12679HexamethylphosphoramideHCID 689053702-Methoxy-6-dodecanoylnaphthalene

Product 1

HCID 1049831-(6-(Dimethylamino)-2-naphthalenyl)-1-dodecanoneYield 66%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Li (0.5 g, 70 mmol) was added to HMPA (20 ml) and benzene (30 ml), and then dimethylamine (3.5 g, 78 mmol) was added dropwise thereto. The mixture was violently stirred for one hour. To the resulting mixture was added 2-methoxy-6-dodecanoylnaphthalene (7.3 g, 22 mmol) prepared in Comparative Example 1-(1) all at one time. The mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into ice-water, extracted with ether, evaporated to remove the solvents, and recrystallized from ethanol to give Laurdan (5.1 g, yield: 66%).

Workup

  1. stirringThe mixture was stirred at room temperature for 5 hours
  2. extractionextracted with ether
  3. customevaporated
  4. customto remove the solvents
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a0f61b78c625438bb6a9ed18d1ebb3d2
Source dataset
uspto-grants-2009_03
Patent number
US07511167B2

Reaction notes

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