Triethylamine → 2.2'-[(methylimino)dibutane-4,1-diyl]bis(1H-isoindole-1.3(2H)-dione)

HRID 908676Notes

Reaction equation

[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=[O:17].C(N(CC)CC)C.Br[CH2:26][CH2:27][CH2:28][CH2:29][N:30]1[C:38](=[O:39])[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]1=[O:40]>O1CCCC1>[CH3:1][N:2]([CH2:26][CH2:27][CH2:28][CH2:29][N:30]1[C:38](=[O:39])[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]1=[O:40])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:8](=[O:17])[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:15]1=[O:16]

Participants

Conditions

Temperature: 165 °C

Procedure

209 mg (0.9 mmol) of 2-[4-(methylamino)butyl]-1H-isoindole-1.3(2H)-dione is solubilized in 5 ml of tetrahydrofuran, then 385 μl (2.7 mmol; 3 equivalents) of triethylamine and 254 mg (0.9 mmol; 1 equivalent) of 2-(4-bromobutyl)-1H-isoindole-1.3(2H)-dione are added to the reaction mixture which is maintained for 25 minutes under microwaves at 165° C. The precipitate obtained is filtered and the filtrate concentrated under reduced pressure. The expected product is purified by chromatography on a silica column (eluent: dichloromethane/methanol: 95/5).

Workup

customThe precipitate obtained
filtrationis filtered
concentrationthe filtrate concentrated under reduced pressure
customThe expected product is purified by chromatography on a silica column (eluent: dichloromethane/methanol: 95/5)

Sources & evidence

ORD record: ord-0b6e342cbe124722bfcbc667e20f65ef
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017637B2

Reaction notes

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