Diallylamine → HCID 90112871, compound

HRID 521708Notes

Reaction equation

Br.Br[CH2:3][C:4]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:5].[CH2:12]([NH:15][CH2:16][CH:17]=[CH2:18])[CH:13]=[CH2:14].C(N(C(C)C)CC)(C)C>O1CCCC1>[CH2:12]([N:15]([CH2:16][CH:17]=[CH2:18])[CH2:3][C:4]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:5])[CH:13]=[CH2:14]

Participants

Conditions

Temperature: 0 °C

Procedure

2-Bromo-1-(3-pyridyl)ethanone hydrobromide (10 g, 23.49 mmol) is added portion wise over 5 minutes to a stirred solution of diallylamine (5.2 mL, 42.29 mmol) and diisopropylethylamine (10.24 mL, 58.73 mmol) in tetrahydrofuran (150 mL) at 0° C. The resulting mixture is stirred at 0° C. for 1 hour. The reaction is quenched by addition of a saturated aqueous solution of sodium bicarbonate (100 mL) and dichloromethane (300 mL). The layers are separated and the aqueous phase is re-extracted with dichloromethane (300 mL). The combined organic layers are dried over magnesium sulfate and the solvents are removed under reduced pressure to give a crude product which is purified by silica gel column chromatography using a 0-5% gradient of 0.14 M ammonia/methanol solution in dichloromethane to give the title compound (4.75 g, 93%). ES/MS (m/e): 217 (M+1).

Workup

customThe reaction is quenched by addition of a saturated aqueous solution of sodium bicarbonate (100 mL) and dichloromethane (300 mL)
customThe layers are separated
extractionthe aqueous phase is re-extracted with dichloromethane (300 mL)
dry with materialThe combined organic layers are dried over magnesium sulfate
customthe solvents are removed under reduced pressure
customto give a crude product which
customis purified by silica gel column chromatography

Sources & evidence

ORD record: ord-53d443787a7c4451a072f988f68f97d0
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328124B2

Reaction notes

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