Chlorobenzene → HCID 57495494, compound

HRID 2266982Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.CC([O-])(C)C.[Na+]>O1CCOCC1>[NH:13]1[CH2:14][CH2:15][CH:10]([CH2:9][NH:8][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:11][CH2:12]1

Participants

Conditions

Temperature: 80 °C

Procedure

Following general procedure F, a mixture of chlorobenzene (102 μL, 1.0 mmol), 4-(aminomethyl)piperidine (137 mg, 1.2 mmol), NaOt-Bu (192 mg, 2.0 mmol), 10 (8 mg, 1 mol %), 1 (5 mg, 1 mol %), and dioxane (1 mL) was heated to 80° C. for 15 h. The crude product was purified via the Biotage SP4 (silica-packed 50 g snap; 7-9% MeOH/CH2Cl2) to provide the title compound as a white solid (159 mg, 84%), mp 60-61° C. 1H NMR (300 MHz, DMSO) δ: 7.02 (t, J=7.5 Hz, 2H), 6.52 (d, J=8.0 Hz, 2H), 6.46 (t, J=8.0 Hz, 1H), 5.58 (s, 1H), 3.11 (s, 1H), 2.92 (d, J=11.5 Hz, 2H), 2.82 (t, J=6.0 Hz, 2H), 2.41 (t, J=10 Hz, 2H), 1.64 (m, 3H), 1.02 (m 2H) ppm. 13C NMR (75 MHz, DMSO) δ: 149.8, 129.5, 115.8, 112.5, 50.0, 46.5, 36.2, 31.7 ppm. IR (neat, cm−1): 3326, 2919, 1602, 1509, 1427, 1325, 1263, 749, 694.

Workup

customThe crude product was purified via the Biotage SP4 (silica-packed 50 g snap; 7-9% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-315187e0d5df4d11985bcefdbeeb38a1
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858784B2

Reaction notes

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