3,4-Dihydroxybenzaldehyde → bis-[N-(3,4-diacetoxybenzyl)tropanium-3-yl] succinate dibromide

HRID 650613Notes

Reaction equation

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

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 5.0 g (13.7 mmol) of bis-tropan-3-yl succinate in 100 mL of dry acetone is added 9.8 g (34.3 mmol) of 3,4-diacetoxybenzyl bromide (prepared from 3,4-dihydroxybenzaldehyde through acetylation of the hydroxy groups, reduction of the aldehyde to the corresponding alcohol, and bromination). Then the mixture is heated at 60-70° C. for 10 hours. The precipitate is collected by filtration, washing with acetone and ether, and drying under vacuum to yield 9.6 g (75%) of bis-[N-(3,4-diacetoxybenzyl)tropanium-3-yl] succinate dibromide as a white powder, which is further purified by recrystallization with methanol-methylene chloride.

Workup

filtrationThe precipitate is collected by filtration
washwashing with acetone and ether
customdrying under vacuum

Sources & evidence

ORD record: ord-a5c212f1fda642369d8a67a113ab5451
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06274623B1

Reaction notes

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