Benzylamine → 40571-86-6

A mixture of cyclohexene oxide (1) (19 mL, 0.2 mol, Aldrich cat #C10,280-4) and benzylamine (27) (21 mL, 0.2 mol, Aldrich cat #407712) in water (5 mL) was refluxed for 3 hours. The cooled reaction mixture was partitioned between 4M aq NaOH (100 mL) and methyl t-butyl ether (150 mL). The aqueous layer was further extracted with methyl t-butyl ether (2×100 mL), and the combined organic extracts were dried over anhydrous magnesium sulfate and concentrated in vacuo to give trans-2-benzylaminocyclohexan-1-ol (28) as a low melting point solid (39.4 g, 96% yield); 1H-NMR (300 MHz, CDCl3) δ: 7.31-7.22 (m, 5H, Ar), 3.91 (d, J 13 Hz, 1H, CH2aN), 3.65 (d, J 13 Hz, 1H, CH2bN), 3.18 (dt, J 5 Hz, J 10 Hz, CH), 2.28 (dt, J 5 Hz, J 10 Hz, CH), 2.15-2.10 (m, 1H, CH), 2.00-1.94 (m, 1H, CH), 1.70-1.60 (m, 2H, CH2), 1.31-1.12 (m, 3H, CH2 & CH), 1.03-0.90 (m, 1H, CH); 13C-NMR (75 MHz, CDCl3) δ: 140.44 (+), 128.31 (−), 128.00 (−), 126.87 (−), 73.62 (−), 62.97 (−), 50.71 (+), 33.35 (+), 30.36 (+), 24.96 (+), 24.28 (+), 19.32 (+).

1. temperaturewas refluxed for 3 hours
2. customThe cooled reaction mixture
3. customwas partitioned between 4M aq NaOH (100 mL) and methyl t-butyl ether (150 mL)
4. extractionThe aqueous layer was further extracted with methyl t-butyl ether (2×100 mL)
5. dry with materialthe combined organic extracts were dried over anhydrous magnesium sulfate
6. concentrationconcentrated in vacuo

ORD record

ord-dcd99f6ea3674ff1a9ccfda46220a924

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115081B2