1-Propanamine, N,N-dimethyl-2,3-bis[(9Z)-9-octadecenyloxy]- → (2,3-Bis-octadec-9-enyloxypropyl)-(3,6,9-trioxodecyloxycarbonylbutyl)-dimethylammonium bromide

HRID 1056464Notes

Reaction equation

[CH2:1]([O:19][CH:20]([CH2:25][O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]=[CH:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:21][N:22]([CH3:24])[CH3:23])[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].[O:45]=[C:46]([CH2:57][CH2:58][C:59](=[O:65])[CH2:60][CH2:61][C:62](=[O:64])[CH3:63])[CH2:47][CH2:48][O:49][C:50](=[O:56])[CH2:51][CH2:52][CH2:53][CH2:54][Br:55]>CC(C)=O>[Br-:55].[CH2:1]([O:19][CH:20]([CH2:25][O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]=[CH:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:21][N+:22]([CH2:54][CH2:53][CH2:52][CH2:51][C:50]([O:49][CH2:48][CH2:47][C:46](=[O:45])[CH2:57][CH2:58][C:59](=[O:65])[CH2:60][CH2:61][C:62](=[O:64])[CH3:63])=[O:56])([CH3:24])[CH3:23])[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

Conditions

Temperature: 80 °C

Procedure

A mixture of 4 (430 mg, 0.69 mmol) and 6 (252 mg, 0.8 mmol) in acetone (5 ml) was stirred in a sealed-tube at RT for 24 h and than at 80° C. for another 24 h. After cooling, the solvent was evaporated in vacuo. Purification by flash chromatography on silica (10% methanol in dichloromethane) gave ME53 as an orange oil (264 mg, 44%).

Workup

temperatureAfter cooling
customthe solvent was evaporated in vacuo
customPurification by flash chromatography on silica (10% methanol in dichloromethane)

Sources & evidence

ORD record: ord-79f437c7fc2c44a199d282ec9feac429
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399016B2

Reaction notes

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