N,N-Dimethylpropargylamine → HCID 68213355, compound

HRID 537843Notes

Reaction equation

HRID 537843 reaction equation
[CH2:1]([CH:19]([N:38]=[N+:39]=[N-:40])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH3:41][N:42]([CH3:46])[CH2:43][C:44]#[CH:45].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>O.C(O)(C)(C)C>[CH3:18][CH2:17][CH2:16][CH2:15][CH2:14]/[CH:13]=[CH:12]\[CH2:11]/[CH:10]=[CH:9]\[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][CH:19]([N:38]1[CH:45]=[C:44]([CH2:43][N:42]([CH3:46])[CH3:41])[N:40]=[N:39]1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

6

Reactant 3

HCID 81643N,N-DimethylpropargylamineHCID 23667548Sodium AscorbateHCID 58559553HCID 58559553, compound

Product 1

HCID 68213355HCID 68213355, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6386tert-ButanolSolvent

Procedure

A solution of dilinoleyl methyl azide (500 mg, 0.90 mmol) and 3-dimethylamino-1-propyne (75 mg, 0.90 mmol) in H2O and tert-butyl alcohol (1:1, 12 mL) was treated with sodium ascorbate (0.090 mmol, 17.94 taken from a 1M solution in water), followed by CuSO4.5H2O (2.3 mg, dissolved in 30 μL of water) and stirred (96 h). The solution was then diluted with H2O (50 mL) and extracted with CH2Cl2 (3×), dried (Na2SO4), filtered, concentrated and purified via column chromatography (2%→4% MeOH/CH2Cl2) to yield the title compound as a colorless oil (524 mg, 91%). 1H NMR (400 MHz, CDCl3, δH) 7.76 (br. s, 1H), 5.47-5.25 (m, 8H), 4.48 (p, 1H), 3.80 (br. s, 2H), 2.75 (app. t, 4H), 2.49 (s, 6H), 2.15-2.00 (m, 8H), 1.91-1.75 (m, 4H), 1.40-1.12 (m, 34H), 1.11-0.98 (m, 2H), 0.85 (t, 6H). FW 637.08, C42H76N4.

Workup

  1. extractionextracted with CH2Cl2 (3×)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified via column chromatography (2%→4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-cdd8abd5cf8d4ab39669bc7054855572
Source dataset
uspto-grants-2014_10
Patent number
US08865675B2

Reaction notes

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