Dibenzylamine → HCID 66587380, compound

HRID 1522956Notes

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.C1(N(CCCC)C2CCCCC2)CCCCC1.C(=O)CCC=C.C1(N(C2CCCCC2)[CH:46]([CH:53]([O:56][CH3:57])[O:54][CH3:55])[CH2:47][CH2:48][C:49](OC)=O)CCCCC1>>[CH2:9]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:46]([CH2:47][CH:48]=[CH2:49])[CH:53]([O:56][CH3:57])[O:54][CH3:55])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Reactant 4

HCID 7656Dibenzylamine

HCID 164184-Pentenal

HCID 12585899HCID 12585899, compound

HCID 49871675HCID 49871675, compound

Product 1

HCID 66587380HCID 66587380, compoundYield 63%

Procedure

The product was prepared by above general procedure and the same chemicals except employing dibenzylamine (1a′) (98 mg, 0.5 mmol), and pent-4-enal (2d′) (63 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 3d as a light yellowish oil (0.102 g, 63% yield); Rf=0.70 (hexane:ethyl acetate=3:1); 1H NMR (CDCl3, 400 MHz) δ 7.38-7.37 (m, 4H), 7.30-7.26 (m, 4H), 7.21-7.18 (m, 2H), 5.89-5.79 (m, 1H), 5.08-5.00 (m, 2H), 4.39-4.38 (d, J=4.93 Hz, 1H), 3.80-3.71 (m, 4H), 3.35 (s, 3H), 3.28 (s, 3H), 2.89-2.84 (m, 1H), 2.44-2.26 (m, 2H) ppm; C NMR (CDCl3, 100 MHz) δ 140.5 (C×2), 137.8, 129.0 (CH×4), 128.0 (CH×4), 126.7 (CH2×2), 115.5, 107.0, 57.8, 54.7, 54.5, 54.4 (CH2×2), 31.2 ppm; FTIR (neat): v=3015, 1454, 1215, 754, 700, 494 cm−1; HRMS (ESI, m/z): calcd for C21H28NO2+ [M+H]+ 326.2120, found: 326.2114.

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-6d73af15d6904731ac43a2f296f9b7da
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079824B2

Reaction notes

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