Dodecylamine → n-Dodecyl amide

HRID 333504Notes

Reaction equation

HRID 333504 reaction equation
[CH3:1][C@@:2]12[CH:11]3[CH2:12][CH:13]=[C:14]4[C@@H:19]5[CH2:20][C:21]([CH3:25])([CH3:24])[CH2:22][CH2:23][C@:18]5([C:26]([OH:28])=[O:27])[CH2:17][CH2:16][C@@:15]4([CH3:29])[C@:10]3([CH3:30])[CH2:9][CH2:8][C@H:7]1[C@@:6]([OH:32])([CH3:31])[C@@H:5]([OH:33])[CH2:4][CH2:3]2.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:67]([NH2:79])[CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH3:78]>C1COCC1.C(Cl)(Cl)Cl.C1CCCCC1.C(OC(=O)C)C>[CH2:67]([NH-:79])[CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH3:78].[CH3:1][C@@:2]12[CH:11]3[CH2:12][CH:13]=[C:14]4[C@@H:19]5[CH2:20][C:21]([CH3:24])([CH3:25])[CH2:22][CH2:23][C@:18]5([C:26]([OH:28])=[O:27])[CH2:17][CH2:16][C@@:15]4([CH3:29])[C@:10]3([CH3:30])[CH2:9][CH2:8][C@H:7]1[C@@:6]([OH:32])([CH3:31])[C@@H:5]([OH:33])[CH2:4][CH2:3]2

Participants

9

Reactant 4

HCID 13583DodecylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 44451366(4aS,6aS,6bR,8aR,9S,10S,12aR,14bS)-9,10-dihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Product 2

HCID 21259697n-Dodecyl amideHCID 44451366(4aS,6aS,6bR,8aR,9S,10S,12aR,14bS)-9,10-dihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolventHCID 21867204Cyclohexane ethylacetateSolvent

Procedure

Gypsogenin (1.30 g, 2.76 mmol) was dissolved in dry THF (40 mL) under argon atmosphere at room temperature. DIEA (1.5 ML, 8.28 mmol) and HBTU (1.30 g, 3.31 mmol) were added to the above solution and reaction mixture was stirred for 1 hr at room temperature to produce an intermediate complex. Dodecylamine (614 mg, 3.31 mmol) was added to the reaction mixture which was further stirred for 48 hours at room temperature. TLC using cyclohexane-ethylacetate (1:1) as mobile phase showed the completion of reaction. The reaction was diluted with chloroform, washed with water, dried over sodium sulfate and concentrated to a solid. Column chromatographic purification of crude product on silica gel G using cyclohexane-ethylacetate (3:1 to 2:1) as mobile phase gave pure dodecylamide derivative of gypsogenin in 65% yield. m.p. 85-87° C.

Workup

  1. customto produce an intermediate complex
  2. stirringwas further stirred for 48 hours at room temperature
  3. customthe completion of reaction
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to a solid
  7. customColumn chromatographic purification of crude product on silica gel G

Sources & evidence

ORD record
ord-e536faa079ac405fa234c525cd0b3a9c
Source dataset
uspto-grants-2014_11
Patent number
US08883170B2

Reaction notes

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