2-Chlorotoluene → HCID 12135563, compound

HRID 2266975Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].[CH2:9]([NH2:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].CC([O-])(C)C.[Na+].O(CCCC)CCCC>>[CH2:9]([NH:15][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

Reactant 4

HCID 72382-Chlorotoluene

HCID 8102Hexylamine

HCID 8909Butyl ether

HCID 23676156Sodium t-butoxide

Product 1

HCID 12135563HCID 12135563, compoundYield 91%

Conditions

Temperature: 85 °C

Procedure

Following general procedure D, a mixture of 2-chlorotoluene (1.17 mL, 10 mmol), hexylamine (1.82 mL, 14 mmol), NaOt-Bu (1.15 g, 12 mmol), 10 (4 mg, 0.05 mol %), 1 (2.5 mg, 0.05 mol %), and Bu2O (3 mL) was heated to 85° C. for 1 h. The crude product was purified via the Biotage SP4 (silica-packed 50 g snap; 0-50% EtOAc/hexanes) to provide the title compound as a clear oil (1.732 g, 91%). 1H NMR (300 MHz, CDCl3) δ: 7.33 (t, J=7.5 Hz, 1H), 7.25 (d, J=7.5 Hz, 1H), 6.83 (m, 2H), 3.61 (s, 1H), 3.33 (t, J=7.0 Hz, 2H), 2.32 (s, 3H), 1.85 (septet, J=7.0 Hz, 2H), 1.58 (m, 6H), 1.14 (t, J=7.0 Hz, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ: 146.8, 130.4, 127.6, 122.0, 117.0, 110.0, 44.4, 32.2, 30.0, 27.4, 23.2, 17.9, 14.5 ppm. IR (neat, cm−1): 3430, 2956, 2924, 2856, 1607, 1514, 1473, 1317, 1260, 745. Anal. Calcd. for C13H21N: C, 81.61; H, 11.06. Found: C, 81.81; H, 11.02.

Workup

customThe crude product was purified via the Biotage SP4 (silica-packed 50 g snap; 0-50% EtOAc/hexanes)

Sources & evidence

ORD record: ord-dc28f45dbadf40e1aec52aa3a05f6b83
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858784B2

Reaction notes

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