Br[CH2:2][C:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=1.[NH2:9][CH2:10][CH2:11][OH:12]>ClC=C(Cl)Cl.[OH-].[Na+]>[OH:12][CH2:11][CH2:10][NH:9][CH2:2][C:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=1A solution of 1-bromomethyl-1-cyclohexene (3.25 g) and 2-aminoethanol (6 mL) in trichloroethylene (40 mL) was heated at the reflux temp. for 3 d, cooled to room temp., and diluted with a 1N NaOH solution (30 mL). The aqueous layer was extracted with CH2Cl2 (4×20 mL) and the combined organic layers were washed with H2O (30 mL) and a saturated NaCl solution (30 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by vacuum distillation to give N-hydroxyethyl-N-cyclohex-1-enylmethylamine as a colorless oil (1.78 g, 62%): bp 92-94° C. (6 mmHg),
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