Benzylamine → N-Benzyl-4-methoxyaniline

HRID 2266972Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CC([O-])(C)C.[Na+].O(CCCC)CCCC>>[CH2:10]([NH:17][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Reactant 4

HCID 7504Benzylamine

HCID 8909Butyl ether

HCID 121674-Chloroanisole

HCID 23676156Sodium t-butoxide

Product 1

HCID 519413N-Benzyl-4-methoxyanilineYield 97%

Conditions

Temperature: 85 °C

Procedure

Following general procedure D, a mixture of 4-chloroanisole (1.23 mL, 10 mmol), benzylamine (1.52 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 25+M; 0-50% EtOAc/hexanes) to provide the title compound as a yellow oil (2.059 g, 97%). 1H NMR (300 MHz, CDCl3) δ: 7.63-7.52 (m, 5H), 7.06 (d, J=9.0 Hz, 2H), 6.81 (d, J=9.0 Hz, 2H), 4.46 (s, 2H), 4.05 (s, 1H), 3.92 (s, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ: 152.6, 143.1, 140.5, 129.2, 128.1, 127.7, 115.4, 114.6, 56.1, 49.5 ppm. IR (neat, cm−1): 3414, 3029, 2832, 1513, 1453, 1235, 1036, 820, 743, 698. Anal. Calcd. for C14H15NO: C, 78.84; H, 7.09. Found: C, 78.61; H, 7.10.

Workup

customThe crude product was purified via the Biotage SP4 (silica-packed 25+M; 0-50% EtOAc/hexanes)

Sources & evidence

ORD record: ord-2253b4c8c999460eaaf47a492c0de062
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858784B2

Reaction notes

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