Allyl bromide → HCID 86719552, compound

HRID 2208793Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:23]([O:25][CH3:26])=[O:24])[C:5]([CH3:22])=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:7]=1.[H-].[Na+].Br[CH2:30][CH:31]=[CH2:32]>CN(C=O)C>[CH2:32]([N:8]([C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]([C:23]([O:25][CH3:26])=[O:24])[C:5]=1[CH3:22])[CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:11][CH2:10]1)[CH:31]=[CH2:30]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of tert-butyl 4-((5-chloro-3-(methoxycarbonyl)-2-methylphenyl)amino)piperidine-1-carboxylate (0.70 g, 1.82 mmol) in DMF (7 mL), was added NaH (0.052 g, 2.19 mmol) at 0° C. After stirring for 20 minutes, 3-bromoprop-1-ene (0.44 g, 3.64 mmol) was added and the mixture was heated at 80° C. for 15 h. On completion, the reaction mass was quenched with ice cold water and extraction was carried out using DCM. The combined organic layers were dried, concentrated under reduced pressure and the residue was purified by column chromatography to afford the title compound (0.3 g, 39%).

Workup

customOn completion, the reaction mass was quenched with ice cold water and extraction
customThe combined organic layers were dried
concentrationconcentrated under reduced pressure
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-2de09686e4d34f1398429d9f86aeabb8
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376422B2

Reaction notes

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