Cyclohexaneethanamine, hydrochloride (1:1)

To a stirred solution of 2-(cyclohex-1-en-1-yl) ethanamine 260 (500 mg, 4.00 mmol) in MeOH (10 mL) under argon atmosphere was added 10percent Pd/C (50 mg) at RT and stirredunder hydrogen atmosphere (balloon pressure) for 16 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was filtered through celite, washed with MeOH (2 x 5 mL) and the filtrate was concentrated in vacuo. The residue was triturated withCH2C12: EtOAc (1: 1, 2 mL), diethyl ether in 1 N HC1(4 mL) to afford compound 261 (250 mg, 38percent) as white solid. TLC: 20percent EtOAc/ hexanes (R 0.3); 1H-NMR (DMSO-d6, 500 MHz): ö7.79 (br s, 2H), 2.77 (t, J 7.5 Hz, 2H), 1.66-1.59 (m, 5H), 1.45-1.41 (m, 2H), 1.32-1.28 (m, 1H), 1.23-1.11 (m, 3H), 0.91-0.84 (m, 2H).General procedure: Appropriate N-substituted phthalimide (5 mmol) and hydrazine hydrate (5 mmol, 0.3 g) in 20 mL of EtOH were refluxed for 3 h. The suspension was cooled, filtered, acidified with hydrochloric acid, and once more filtered. The filtrate was concentrated under reduced pressure and the products were crystallized as hydrochloride salts from Et(b) (2-Cyclohexylethyl) amine, hydrochloride salt; A solution of the compound from Example 92a) (23. 8 g ; 0.092 mol. ) and hydrazine hydrate (5.0 mL; 1.1 equiv.) in methanol (250 mL) was stirred and heated under reflux for 3h. The mixture was cooled and evaporated and the residue slurried with diethyl ether (500 mL) and filtered. The filtrate was then evaporated and dissolved in diethyl ether (200 mL) then the solution saturated with gasous hydrochloric acid. The mixture was filtered to afford the title compound (1.7 g ; 14percent) as a yellow powder. 1H NMR (400 MHz, DMSO-d6) 8 ppm 0.83-1. 67 (m, 13 H), 2.72-2. 80 (m, 2 H), 8.02 (br s, 3 H).A solution of the compound from Example 92a) (23.8 g; 0.092 mol.) and hydrazine hydrate (5.0 mL; 1.1 equiv.) in methanol (250 mL) was stirred and heated under reflux for 3h. The mixture was cooled and evaporated and the residue slurried with diethyl ether (500 mL) and filtered. The filtrate was then evaporated and dissolved in diethyl ether (200 mL) then the solution saturated with gasous hydrochloric acid. The mixture was filtered to afford the title compound (1.7 g; 14percent) as a yellow powder. 1 H NMR (400 MHz, DMSOdA solution of dicyclohexylcarbodiimide (DCC) (120 mg, 0.58 mmol) in THF (2 mL) was added to a solution of HOBt (72 mg, 0.54 mmol) and 7-hydroxy-Boc- D-Tic(OH) (150 mg, 0.51 mmol) in THF (3 mL). After 1 h, the 2-cyclohexylethylamine (AZ1) hydrochloride (96 mg, 0.6 mmol) and NEt3 (0.25 mL, 1.7 mmol) were added to the suspension. The reaction mixture was stirred at room temperature for 12 h. The solids were removed by filtration, and the filtrate concentrated to a residue. The residue was subjected to chromatography on silica gel eluting with a gradient up to 50% EtOAc in hexanes. The product containing fractions were concentrated and the residue dissolved in CH3OH (5 mL) and treated with 4 N HCl in dioxane (5 mL). After 12 h, the solution was concentrated and the residue partitioned between EtOAc and aq. NaHC03. The organic layer was dried (Na2S04) and concentrated. The residue was subjected to chromatography on silica gel eluting with a gradient up to 100% EtOAc in hexanes to afford the freebase (55): lH NMR (300 MHz, CD3OD) delta 8.38 (br. s., 1H), 7.08 (d, = 8.48 Hz, 1H), 6.75 (dd, / = 2.45, 8.48 Hz, 1H), 6.63 (s, 1H), 4.33 (s, 2H), 4.11 (dd, / = 4.80, 11.77 Hz, 1H), 3.53- 3.78 (m, 1H), 3.22 (d, = 4.71 Hz, 1H), 2.92-3.13 (m, 1H), 1.60-1.82 (m, 6H), 1.07-1.53 (m, 7H), 0.80-1.06 (m, 2H); 13C NMR (75 MHz, CD3OD) delta 169.5, 169.4, 158.1, 131.1, 129.7, 122.1, 116.9, 113.7, 56.9, 45.6, 38.5, 38.4, 37.8, 36.5, 34.3, 34.2, 30.4, 27.6, 27.3. The free base was converted into 50 mg (28%) of an off-white powder as the hydrochloride salt (55) · HCl: MS (ESI) mlz 303.1 (M + H)+; m.p. 78-82 C (fusion); [ ]D25 = +99 (c 0.32, CH3OH). Anal. (Ci8H27ClN2O2 FontWeight='Bold' FontSize='10' 0.75H2O) C, H, N.General procedure: To the solution of trichloromethyl chloroformate (0.6 g, 3 mmol) and the catalytic amount of activated charcoal in 20 mL of dry ethyl acetate was added rapidly the corresponding amine hydrochloride (2.5 mmol) in 10 mL of dry ethyl acetate. The reaction mixture was heated to reflux for 4-5 h, the black solution was cooled and filtered, and the solvent was evaporated carefully under reduced pressure. The freshly prepared isocyanate was dissolved in 20 mL of dry acetonitrile and added to a mixture of 3-(1H-imidazol-4-yl)propanol hydrochloride (2.5 mmol, 0.4 g) in 10 mL of dry acetonitrile. The solution was refluxed for 4-5 h and concentrated in vacuo. The residue was purified by rotatory chromatography [eluent: CH2Cl2/MeOH (gradient from 99:1 to 90:10), ammonia atmosphere]. Separation was monitored by TLC. The products were obtained as colorless oils and crystallized as hydrogen maleates in Et2O/EtOH.

Mainly used as a metal cleaning agent, a dry cleaning agent for textiles, but also as an adhesive, metal cutting additive and polymerization solvent for DAP resin, etc.

Molecular Weight:163.69
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:163.1127773
Monoisotopic Mass:163.1127773
Topological Polar Surface Area:26
Heavy Atom Count:10
Complexity:65
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes