Benzylamine → 40571-86-6

HRID 1045670Notes

Reaction equation

[CH:1]12[O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH2:8]([NH:15][C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C@H:1]1[OH:7])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Reactant 2

HCID 7504Benzylamine

HCID 9246Cyclohexene oxide

Product 1

HCID 272465040571-86-6Yield 62.3%

Conditions

Temperature: 80 °C

Procedure

A mixture of cyclohexene oxide (20 g, 204 mmol) and benzylamine (44 g, 411 mmol) was heated at 80° C. for 6 hours. An excess benzylamine was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent; 5-10% methanol in chloroform) to afford (1RS,2RS)-trans-2-benzylaminocyclohexanol (26 g, 127 mmol, 62%) as white crystals.

Workup

customAn excess benzylamine was removed under reduced pressure
customthe residue was purified by silica gel column chromatography (eluent; 5-10% methanol in chloroform)

Sources & evidence

ORD record: ord-58020261d6ce4e3b8a5541c81c14f670
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569294B2

Reaction notes

Loading…