1,3-Cyclohexadiene → HCID 58975559, compound

HRID 606663Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH2:11][CH2:12][NH:13][CH2:14][C:15]1[CH:16]=[C:17]([C:21]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:22])[CH:18]=[CH:19][CH:20]=1)([O-])=O.C1CCC=CC=1>CCO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH2:11][CH2:12][NH:13][CH2:14][C:15]1[CH:16]=[C:17]([C:21]([N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)=[O:22])[CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (3-{[2-(2-nitro-phenylamino)-ethylamino]-methyl}-phenyl)piperidin-1-yl-methanone (Example 11; 0.060 g, 0.16 mmol) in EtOH (1.6 mL) was added cyclohexadiene (0.55 mL) followed by Pd/C (10 wt %, 0.02 g), and the resulting suspension was heated to 100° C. for 45 min. The suspension was filtered (diatomaceous earth), and the filtrate was concentrated under reduced pressure. The crude residue was purified by column chromatography (0-5% CH3OH/CH2Cl2) to provide the desired product as a colorless oil (0.034 g, 61%). MS (ESI): mass calculated for C21H28N4O, 352.23; m/z found, 353.2 [M+H]+, 375.2 [M+Na]+. 1H NMR (400 MHz, CDCl3): 7.38-7.32 (m, 3H), 7.26-7.24 (m, 1H), 6.80 (d t, J=5.4, 1.9 Hz, 1H), 6.72-6.64 (m, 3H), 3.84 (br s, 2H), 3.70 (br s, 2H), 3.32 (br s, 2H), 3.21 (t, J=5.7 Hz, 2H), 2.94 (t, J=5.7 Hz, 2H), 1.67 (br s, 4H), 1.50 (br s, 1H). 13C NMR (100 MHz, CDCl3): 170.3, 140.7, 137.7, 136.7, 134.6, 129.1, 128.4, 126.5, 125.3, 120.5, 118.7, 116.3, 112.0, 53.3, 48.1, 43.8, 29.7, 26.5, 24.6.

Workup

filtrationThe suspension was filtered (diatomaceous earth)
concentrationthe filtrate was concentrated under reduced pressure
customThe crude residue was purified by column chromatography (0-5% CH3OH/CH2Cl2)

Sources & evidence

ORD record: ord-9c01ea783d0245439b12c2497fbcb961
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915420B2

Reaction notes

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