4-(Bromoheptyl)-2,6-dimethyl pyridine → 4-(7-Phthalimidoheptyl)-2,6-dimethylpyridine

HRID 365700Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([CH3:16])[CH:10]=1.[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.[K]>CN(C)C=O>[C:17]1(=[O:27])[N:21]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]2[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([CH3:16])[CH:10]=2)[C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of compound (14) (3.54 g, 12.5 mmol), potassium phthalimide (2.54 g, 13.7 mmol) and dimethylformamide (25 ml) was heated at 125° C. for 6 h. DMF was evaporated and the residue coevaporated twice with n-butanol and twice with toluene. The dry crude product was purified by flash chromatography. Yield: 3.54 g (81%) viscous oil Rf=0.46 (System A) H1NMR (60 MHz, CDCl3): 7.60-7.95 (m, 4H), 6.76 (s, 2H), 3.68 (t, 2H, J=7 Hz), 2.48 (s, 6H), 2.36-2.60 (m, 2H), 1.23-1.77 (m, 10H)

Workup

customDMF was evaporated
customThe dry crude product
customwas purified by flash chromatography

Sources & evidence

ORD record: ord-77af31aea18d4f189fd4805b7f74bf3b
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127529

Reaction notes

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