Dibenzylamine → HCID 66587526, compound
Reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:16]1(N(CCCC)C2CCCCC2)CCCCC1.CC(C)CC=O.C1(N([CH:52]([CH2:58][CH2:59]CC)[CH:53]([O:56][CH3:57])[O:54][CH3:55])C2CCCCC2)CCCCC1>>[CH2:9]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:52]([CH:58]([CH3:59])[CH3:16])[CH:53]([O:56][CH3:57])[O:54][CH3:55])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1Participants
Procedure
The product was prepared by above general procedure and the same chemicals except employing dibenzylamine (1a′) (98 mg, 0.5 mmol), and 3-methylbutanal (2b′) (64 mg, 0.75 mmol). After 24 h, the crude product was purified by flash column chromatography (silica gel; ethyl acetate or diethyl ether/hexane=1:100) to afford the desired product 3b as a light yellowish oil (0.108 g, 66% yield); Rf=0.76 (hexane:ethyl acetate=3:1); 1H NMR (CDCl3, 400 MHz) δ 7.38-7.36 (m, 4H), 7.30-7.26 (m, 4H), 7.22-7.18 (m, 2H), 4.51-4.50 (d, J=4.28 Hz, 1H), 3.91-3.62 (m, 4H), 3.40 (s, 3H), 3.37 (s, 3H), 2.46-2.43 (m, 1H), 2.05-1.97 (m, 1H), 0.99-0.98 (t, J=6.82 Hz, 3H), 0.84-0.82 (t, J=6.68 Hz, 3H) ppm; 13C NMR (CDCl3, 100 MHz) δ 140.7 (C×2), 129.2 (CH×4), 128.0 (CH×4), 126.6 (CH×2), 107.1, 62.5, 55.5 (CH2×2), 55.5, 54.8, 27.2, 20.9, 20.7 ppm; FTIR (neat): v=3015, 1215, 754, 700, 494 cm−1; HRMS (ESI, m/z): calcd for C21H30NO2+ [M+H]+ 328.2277, found: 328.2273.
Workup
- customThe product was prepared by above general procedure
- customthe crude product was purified by flash column chromatography (silica gel; ethyl acetate or diethyl ether/hexane=1:100)
Sources & evidence
- ORD record
- ord-fc46963d52924721811008ffca840bd0
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079824B2
Reaction notes
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