Benzylamine → Benzylaniline

HRID 2266974Notes

Reaction equation

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

Participants

Reactant 4

HCID 7504Benzylamine

HCID 7964Chlorobenzene

HCID 8909Butyl ether

HCID 23676156Sodium t-butoxide

Product 1

HCID 66028BenzylanilineYield 90%

Conditions

Temperature: 85 °C

Procedure

Following general procedure D, a mixture of chlorobenzene (1.02 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 (1.646 g, 90%). 1H NMR (300 MHz, CDCl3) δ: 7.69-7.61 (m, 5H), 7.53 (t, J=7.5 Hz, 2H), 7.09 (t, J=7.5 Hz, 1H), 6.92 (d, J=7.5 Hz, 2H), 4.57 (s, 2H), 4.22 (s, 1H) ppm. 13C NMR (75 MHz, CDCl3) δ: 148.8, 140.2, 129.9, 129.3, 128.1, 127.8, 118.1, 113.5, 48.7 ppm. IR (neat, cm−1): 3419, 3052, 3026, 2841, 1603, 1506, 1453, 1325, 750, 693. Anal. Calcd. for C13H13N: C, 85.21; H, 7.15. Found: C, 85.04; H, 7.15.

Workup

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

Sources & evidence

ORD record: ord-97dd2d6df90945fc85f7ce9aed6f7ada
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858784B2

Reaction notes

Loading…