3-(2,4-dichlorophenyl)propanal

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Condensation of 15 (550 mg, 1.9 mmol) and 3-(2,4-dichlorophenyl)-propionaldehyde (390 mg, 1.9 mmol) following the procedure described in Example 45, Step 2, followed by conversion to the HCl salt, gave 6-(trans-4-{[3-(2,4-dichlorophenyl)propyl]methylamino}cyclohexyl)-3H-benzoxazol-2-one (446 mg, 50%), as an off-white solid: mp 273-279° C.; IR (KBr): 2949, 1775, 1500, 1474 cm−1; 1H NMR(500 MHz, DMSO-d6): δ 11.49 (s, 1H), 10.01 (s, 1H), 7.61 (d, J=2 Hz, 1H), 7.47-7.41 (m, 2H), 7.17 (s, 1H), 7.00 (s, 2H), 3.34-3.29 (m, 1H), 3.22-3.17 (m, 1H), 3.11-3.03 (m, 1H), 2.79-2.73 (m, 2H), 2.71 (d, J=5 Hz, 3H), 2.59-2.48 (m, 1H), 2.14-2.06 (m, 2H), 2.03-1.97 (m, 2H), 1.94-1.88 (m, 2H), 1.69-1.50 (m, 4H); ESI (m/z): 433 [M+H]+; HPLC: method A, 6.78 minutes (>99%); Anal. Calcd for C23H26Cl2N2O2.HCl: C, 58.80; H, 5.79; N, 5.96. Found: C, 58.62; H, 5.76; N, 5.89.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Condensation of 15 (550 mg, 1.9 mmol) and 3-(2,4-dichlorophenyl)-propionaldehyde (390 mg, 1.9 mmol) following the procedure described in Example 45, Step 2, followed by conversion to the HCl salt, gave 6-(trans-4-{[3-(2,4-dichlorophenyl)propyl]methylamino}cyclohexyl)-3H-benzoxazol-2-one (446 mg, 50%), as an off-white solid: mp 273-279° C.; IR (KBr): 2949, 1775, 1500, 1474 cm−1; 1H NMR(500 MHz, DMSO-d6): δ 11.49 (s, 1H), 10.01 (s, 1H), 7.61 (d, J=2 Hz, 1H), 7.47-7.41 (m, 2H), 7.17 (s, 1H), 7.00 (s, 2H), 3.34-3.29 (m, 1H), 3.22-3.17 (m, 1H), 3.11-3.03 (m, 1H), 2.79-2.73 (m, 2H), 2.71 (d, J=5 Hz, 3H), 2.59-2.48 (m, 1H), 2.14-2.06 (m, 2H), 2.03-1.97 (m, 2H), 1.94-1.88 (m, 2H), 1.69-1.50 (m, 4H); ESI (m/z): 433 [M+H]+; HPLC: method A, 6.78 minutes (>99%); Anal. Calcd for C23H26Cl2N2O2.HCl: C, 58.80; H, 5.79; N, 5.96. Found: C, 58.62; H, 5.76; N, 5.89.

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared according to the previously described general procedure (GP11) by reaction of 2-(2,4-dimethyl-imidazol-1-yl)-ethylamine with 3-(2,4-dichloro-phenyl)-propionaldehyde. LC-MS: tR=0.64 min.; [M+H]+=324 g/mol. Prepared

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Condensation of 15 (550 mg, 1.9 mmol) and 3-(2,4-dichlorophenyl)-propionaldehyde (390 mg, 1.9 mmol) following the procedure described in Example 45, Step 2, followed by conversion to the HCl salt, gave 6-(trans-4-{[3-(2,4-dichlorophenyl)propyl]methylamino}cyclohexyl)-3H-benzoxazol-2-one (446 mg, 50%), as an off-white solid: mp 273-279° C.; IR (KBr): 2949, 1775, 1500, 1474 cm−1; 1H NMR(500 MHz, DMSO-d6): δ 11.49 (s, 1H), 10.01 (s, 1H), 7.61 (d, J=2 Hz, 1H), 7.47-7.41 (m, 2H), 7.17 (s, 1H), 7.00 (s, 2H), 3.34-3.29 (m, 1H), 3.22-3.17 (m, 1H), 3.11-3.03 (m, 1H), 2.79-2.73 (m, 2H), 2.71 (d, J=5 Hz, 3H), 2.59-2.48 (m, 1H), 2.14-2.06 (m, 2H), 2.03-1.97 (m, 2H), 1.94-1.88 (m, 2H), 1.69-1.50 (m, 4H); ESI (m/z): 433 [M+H]+; HPLC: method A, 6.78 minutes (>99%); Anal. Calcd for C23H26Cl2N2O2.HCl: C, 58.80; H, 5.79; N, 5.96. Found: C, 58.62; H, 5.76; N, 5.89.