2-Bromoethanol → HCID 86675881, compound

HRID 1471446Notes

Reaction equation

HRID 1471446 reaction equation
[C:1]([O:20][CH2:21][CH2:22][CH2:23][N:24]([C:48](=[O:53])[CH2:49][N:50]([CH3:52])[CH3:51])[CH2:25][CH2:26][CH2:27][O:28][C:29](=[O:47])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]/[CH:37]=[CH:38]\[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[Br:54][CH2:55][CH2:56][OH:57]>C(#N)C>[Br-:54].[C:1]([O:20][CH2:21][CH2:22][CH2:23][N:24]([CH2:25][CH2:26][CH2:27][O:28][C:29](=[O:47])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]/[CH:37]=[CH:38]\[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C:48](=[O:53])[CH2:49][N+:50]([CH2:55][CH2:56][OH:57])([CH3:52])[CH3:51])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 108982-BromoethanolHCID 72550261HCID 72550261, compound

Product 1

HCID 86675881HCID 86675881, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

In a sealed system, (Z)-((2-(dimethylamino)acetyl)azanediyl)bis(propane-3,1-diyl) dioleate (269 mg, 0.360 mmol) was dissolved in ACN (10 mL) and 2-Bromoethanol (200 uL) was added. The reaction vessel was flushed with inert gas and then sealed. Reaction was heated to 80° C. and allowed to stir overnight. The reaction mixture was cooled and concentrated. Purification by silica gel chromatography with a DCM/MeOH gradient yielded 2-(bis(3-(oleoyloxy)propyl)amino)-N-(2-hydroxyethyl)-N,N-dimethyl-2-oxoethanaminium bromide (129 mg). QTOF MS ESI+: m/z 791.7 (M+H).

Workup

  1. customThe reaction vessel was flushed with inert gas
  2. customsealed
  3. customReaction
  4. temperatureThe reaction mixture was cooled
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography with a DCM/MeOH gradient

Sources & evidence

ORD record
ord-1ee01aa37d6d4398bf25f6615264a720
Source dataset
uspto-grants-2015_04
Patent number
US09011903B2

Reaction notes

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