Isopropanol → HCID 68658003, compound

HRID 1504255Notes

Reaction equation

[CH2:1]([NH:13][C:14](=[O:24])[CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Br:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].C(O)(C)C.C(Cl)(Cl)Cl.CO>CO>[Br-:25].[CH2:1]([NH:13][C:14](=[O:24])[CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][N+:20]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])([CH3:23])[CH2:19][CH2:18]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

Conditions

Temperature: 40 °C

Procedure

N-dodecyl-3-(4-methylpiperazin-1-yl)propanamide 30.0 g (0.088 moles), 1-bromohexane 14.6 g (0.088 moles), and 11.2 g of isopropyl alcohol are charged into a 3-neck 250-mL round bottom flask equipped with a thermocouple, and reflux condenser. The mixture is agitated using a magnetic stirring bar and heated to reflux overnight. Then, the reaction mass is cooled down to about 40° C. and diluted to 40% active solids with 56 g of methanol. Evidence of the chemical transformation is observed by TLC analysis using a 4:1 CHCl3/MeOH as mobile phase. The final product is a light brown solution at ambient temperature. 1H-NMR (300 MHz, CDCl3): δ 3.10 (m, 5H), 2.90 (m, 10H), 2.36 (in, 4H), 1.34 (bs, 2H), 0.80 (in, 26H), 0.44 (m, 6H). 13C-NMR (75 MHz, CDCl3): δ 170.94, 62.39, 59.24, 52.17, 48.35, 45.12, 38.39, 32.50, 30.75, 30.12, 28.52, 28.49, 28.38, 28.18, 28.18, 25.98, 24.85, 24.11, 21.50, 21.28, 20.74, 12.92, 12.74.

Workup

customequipped with a thermocouple
temperaturereflux condenser
temperatureheated
temperatureto reflux overnight

Sources & evidence

ORD record: ord-6d075e56c85b479db64ed58b207ecd43
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212305B2

Reaction notes

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