3-Benzyl-3-azabicyclo[3.2.1]octan-6-one → 3-Benzyl-7-dimethylaminomethylene-3-aza-bicyclo[3.2.1]octan-6-one

HRID 272616Notes

Reaction equation

[CH2:1]([N:8]1[CH2:14][CH:13]2[CH2:15][CH:10]([CH2:11][C:12]2=[O:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC(OC(N(C)C)N(C)C)(C)C>[CH2:1]([N:8]1[CH2:14][CH:13]2[CH2:15][CH:10]([C:11](=[CH:1][N:8]([CH3:14])[CH3:9])[C:12]2=[O:16])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To 3-benzyl-3-aza-bicyclo[3.2.1]octan-6-one (3.2 mmol) was taken up in Brederick's reagent (tris-(N,N-dimethylamino)methane, 10 mL) and heated for 8 h at 100° C. Excess Brederick's was removed in vacuo and the crude product was used as is in subsequent steps. 1H NMR (CDCl3, 400 MHz) δ 7.50 (m, 5H), 3.56 (s, 3H), 2.99 (s, 6H), 2.40–2.20 (m, 4H), 1.95 (m, 2H), 2.56 (m, 2H); APCl MS m/z 271.3 (M+H)+.

Workup

customExcess Brederick's was removed in vacuo

Sources & evidence

ORD record: ord-075a02317da34a38a2960cb70ebc950d
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456177B2

Reaction notes

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