Hexylamine → HCID 12045720, compound

HRID 2266971Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH2:10]([NH2:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].CC([O-])(C)C.[Na+].O(CCCC)CCCC>>[CH2:10]([NH:16][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

Reactant 4

HCID 8102Hexylamine

HCID 8909Butyl ether

HCID 121674-Chloroanisole

HCID 23676156Sodium t-butoxide

Product 1

HCID 12045720HCID 12045720, compoundYield 88.2%

Conditions

Temperature: 85 °C

Procedure

Following general procedure D, a mixture of 4-chloroanisole (1.23 mL, 10 mmol), hexylamine (1.83 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 100 g; 0-50% EtOAc/hexanes) to provide the title compound as a yellow oil (1.828 g, 88%). 1H NMR (300 MHz, CDCl3) δ: 6.84 (d, J=9.0 Hz, 2H), 6.62 (d, J=9.0 Hz, 2H), 3.78 (s, 3H), 3.40 (s, 1H), 3.09 (t, J=7.0 Hz, 2H), 1.64 (pentet, J=7.5 Hz, 2H), 1.42 (m, 6H), 0.97 (t, J=7.0 Hz, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ: 152.2, 143.2, 115.1, 114.2, 56.0, 45.3, 32.0, 30.0, 27.2, 23.0, 14.4 ppm. IR (neat, cm−1): 3394, 2929, 2857, 2831, 1513, 1466, 1237, 1180, 1040, 819, 520.

Workup

customThe crude product was purified via the Biotage SP4 (silica-packed 100 g; 0-50% EtOAc/hexanes)

Sources & evidence

ORD record: ord-5e67ab393b454d91840c53f72fefe5b9
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858784B2

Reaction notes

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