Reaction SMILES: C(#N)C.N1C(C)=CC=[CH:6][C:5]=1[CH3:11].CCN=C=N[CH2:17][CH2:18][CH2:19][N:20]([CH3:22])[CH3:21].Cl.Cl>O.CC(OC)(C)C>[CH3:22][N:20]([CH:19]1[CH2:18][CH2:17][CH2:11][CH2:5][CH2:6]1)[CH3:21]
Reactant: CCN=C=NCCCN(C)C
Reactant: Cc1cccc(C)n1
Agent: Cl
Solvent: O
Solvent: CC#N
Solvent: COC(C)(C)C
Product: CN(C)C1CCCCC1
Temperature: 7.5 °C
Reaction time: 4 h
Yield: 303.1 %

Procedure:
Into a reactor (R-1) was charged 351 kg of compound Ia, 314 kg of compound Ib, and 807 L of acetonitrile. Batch temperature was adjusted to 0 to 10° C. 323 kg of 2,6-lutidine followed by 123 L of acetonitrile was charged to R-1, while maintaining temperature at 0 to 15° C. 351 kg of EDCI-HCl followed by 123 L of acetonitrile was charged to between 5 to 25° C. The mixture was stirred at 20 to 30° C. for 4 h. Reaction completion was checked by HPLC to show less than 0.75% of un-reacted compound Ia. 1755 L of MTBE followed by 807 kg of 9.9% HCl was charged to R-1 between 15° C. to 25° C. The batch was stirred for 15 minutes and settled for at least 30 minutes, and the aqueous layer was split to HOLD TANK. 807 kg of 9.9% HCl was charged to R-1 at 15 to 25° C. The batch was stirred for 15 minutes and settled for 30 minutes, and the aqueous layer was split to HOLD TANK. 211 kg of sodium bicarbonate followed by 4001 L of water was charged to R-2, and the whole was agitated until all solid dissolved. 1404 L of the NaHCO3 solution in R-2 was transferred to R-1 at 15 to 25° C. The mixture was stirred for 15 minutes and settled for at least 30 minutes. The aqueous layer was split to HOLD TANK. 140 kg of sodium chloride was charged to the NaHCO3 solution in R-2. Half of the NaHCO3/NaCl solution in R-2 was transferred to R-1. The whole in R-1 was agitated for 15 minutes and settles for at lest 30 minutes. The aqueous layer was split to HOLD TANK. The remainder of the NaHCO3/NaCl solution in R-2 was transferred to R-1. The whole in R-1 was agitated for 15 minutes and settled for at lest 30 minutes. The aqueous layer was split to HOLD TANK. The batch in R-1 was concentrated to about 1053 L under vacuum. 97 kg of lithium hydroxide Monohydrate followed by 1404 L of water was charged to R-2, and the mixture was stirred at 20 to 30° C. until all solids dissolved. The lithium hydroxide solution in R-2 was transferred to R-1. The whole was stirred at 20 to 30° C. for 3 h. Hydrolysis completion was checked by HPLC to show 100% conversion. 1053 L of MTBE followed by 1404 L of water was charged to R-1. The mixture was stirred for 20 minutes and settles for at least 30 minutes. The aqueous layer was split to R-2. The organic layer was transferred to HOLD TANK. 1053 L of MTBE was charged to R-2. The mixture was stirred for about 10 minutes and settled for at least 30 minutes. The aqueous layer was transferred to R-1. The organic layer was transferred to HOLD TANK. 293 kg of 9.9% HCl followed by 1530 kg of isopropyl acetate and 660 kg of 9.9% HCl was charged to R-1 at 20 to 30° C. The mixture in R-1 was stirred for 30 minutes and settled for at least 30 minutes. The aqueous layer was split to HOLD TANK. 35 kg of Sodium Chloride followed by 702 L of water was charged to R-2. The NaCl solution in R-2 was transferred to R-1. The mixture was stirred for 15 minutes at 15 to 25° C. and settled for at least 30 minutes. The aqueous layer was split to HOLD TANK. The batch in R-1 followed by 306 kg of isopropyl acetate rinse was transferred to R-2 via 1 μm inline filter. The batch in R-2 was concentrated to about 1404 L under vacuum at 35 to 60° C. 918 kg of isopropyl acetate was charged to R-2, and the batch was concentrated to about 1404 L under vacuum at 35 to 60° C. Water content in the batch was <0.5% w/w. 1530 kg of isopropyl acetate was charged to R-2. The batch temperature was adjusted to 43 to 48° C., and 109 kg of N,N-dimethylcyclohexylamine (DMCA) was charged to R-2. 4 kg of compound Ic′ seed in 11 L of isopropyl acetate was charged to R-2. The batch was stirred for 5 h at 43 to 48° C. for 1 h. 130 kg of DMCA was charged to R-2 over 2 h at 43 to 48° C. 153 kg of isopropyl acetate rinse was charged to R-2. The batch was cooled to 5 to 10° C. over a period of 3 hours. The batch was filtered in portions with a centrifuge. The wet cake was washed with cold isopropyl acetate and was dried under vacuum at 25° C. for 4 h followed by at 45° C. for at least 8 h. 706 kg of Compound Ic′ was obtained (90% yield). 1H NMR (DMSO-d6), δ 0.80 (s, 3H), 0.91 (s, 9H), 0.99 (s, 3H), 1.02-1.25 (m, 5H), 1.17 (s, 9H), 1.35 (d, J=8 Hz, 1H), 1.43 (dd, J=5 and 8 Hz, 1H), 1.54-1.58 (m, 1H), 1.68-1.78 (m, 3H), 2.23 (s, 6H), 2.28 (m, 1H), 3.73 (dd, J=5 and 10 Hz, 1H), 3.96 (d, J=10 Hz, 1H), 4.08 (s, 1H), 4.15 (d, J=10 Hz, 1H), 5.87 (d, J=10 Hz, 1H), 5.95 (brs, 1H).