1-Dodecanol → Dodecyl N,N-dimethylglycinate

HRID 2096033Notes

Reaction equation

HRID 2096033 reaction equation
[CH2:1]([OH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(N(CC)CC)C.Cl.[CH3:22][N:23]([CH3:28])[CH2:24][C:25](O)=[O:26].C1(N=C=NC2CCCCC2)CCCCC1>CN(C1C=CN=CC=1)C.CN(C)C=O>[CH2:1]([O:13][C:25](=[O:26])[CH2:24][N:23]([CH3:28])[CH3:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 81931-DodecanolHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 75605N,N-Dimethylglycine hydrochloride

Product 1

HCID 129378Dodecyl N,N-dimethylglycinateYield 48.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

First, 1-dodecyl alcohol (2.98 g, 0.016 mol), triethylamine (1.62 g, 0.016 mol) and 4-(N,N-dimethylamino)pyridine (DMAP; 0.195 g, 0.0016 mol) were added to a solution of N,N-dimethylglycine hydrochloride (2.23 g, 0.016 mol) in dry N,N-dimethylformamide (DMF; 100 mL) under nitrogen atmosphere, and cooled to 0° C. Then, dicyclohexylcarbodiimide (DCC; 3.63 g, 0.0176 mol) in dry DMF (60 ml) was added thereto at 0° C. The reaction mixture was returned to room temperature and stirred for about one day, then DMF was evaporated under reduced pressure with a pump. The residue was dissolved using ether and aqueous saturated sodium bicarbonate solution, and the ether layer was collected and washed once with water and once with saturated saline, after which it was dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The resultant residue was separated by column chromatography (hexane:ethyl acetate:triethylamine=50:50:1) to give N,N-dimethylamino-acetate-1-dodecyl ester (C12-tertiary amine) (yield 48%, 2.10 g).

Workup

  1. customat 0° C
  2. customwas returned to room temperature
  3. customDMF was evaporated under reduced pressure with a pump
  4. dissolutionThe residue was dissolved
  5. customthe ether layer was collected
  6. washwashed once with water and once with saturated saline
  7. dry with materialafter which it was dried over anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe resultant residue was separated by column chromatography (hexane:ethyl acetate:triethylamine=50:50:1)

Sources & evidence

ORD record
ord-53b344398bff487384cd13a4f655d2d3
Source dataset
uspto-grants-2013_05
Patent number
US08449979B2

Reaction notes

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