The origin of a common compound about 6940-76-7

The synthetic route of 1-Chloro-3-iodopropane has been constantly updated, and we look forward to future research findings.

Application of 6940-76-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 6940-76-7, name is 1-Chloro-3-iodopropane belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of (+)-(2S,5R)-1-allyl-2,5-dimethylpiperazine (10.6 g, 68.7 mmol, prepared according to the literature procedure described by Janetka, J.W. et al., J. Org. Chem., 2003, 68, 3976-3980), 1 -chloro-3-iodo-propane (16.9 g, 82.8 mmol, 1.2 eq), and K2CO3 (24.6 g, 178 mmol, 2.6 eq) in acetone (230 mL) was heated at 5O0C for 16 hours. The mixture was cooled to room temperature, filtered through Celite, and the filtrate was concentrated in vacuo. Chromatography on silica gel using a gradient of 2M NHs/MeOH in CH2CI2 (0-2%) gave 14.05 g (89%) of (2S,5fi)-1 -allyl^^S-chloro-propyO^.delta- dimethyl-piperazine as a light yellow oil.To a solution of (2S,5/^-1-allyl-4-(3-chloro-propyl)-2,5-dimethyl-piperazine (14.05 g, 61 mmol) in anhydrous THF (78 mL) under argon was added thiosalicylic acid (10.33 g, 67 mmol, 1.1 eq) followed by the addition of a solution of tris(dibenzylidenacetone)-dipalladium (Pd2(dba)3, 2.8 g, 3.1 mmol, 5 mol%) and1 ,4-bis(diphenylphosphino)butane (DPPB, 1.33 g, 3.1 mmol, 5 mol%) in anhydrous THF (26 mL, pre-mixed for 15 minutes). After stirring at room temperature for 2 hours, the mixture was filtered through Celite. The filtrate was concentrated in vacuo and the residue was partitioned between 1 N aqueous HCI (70 mL) and Et2O (70 mL). The aqueous layer was separated and extracted with Et2O (50 mL x 2), and treated with NaOH (solid) to bring its pH to 13. The aqueous phase was extracted with CHCI3 (50 mL x 4). The combined organic phase was dried (Na2SO4) and concentrated in vacuo EPO to give 11.6 g (100%) of (2S,5/:?)-4-(3-chloro-propyl)-2I5-ciimethyl-piperazine as a light yellow oil.To a solution of (2S,5R)-4-(3-chloro-propyl)-2,5-dimethyl-piperazine (11.6 g, 61 mmol) in CH2CI2 (240 ml_) at O0C was added Boc2O (14.9 g, 67 mmol, 1.1 eq) and the mixture was stirred at room temperature for 16 hours. The solvent was evaporated and the residue was chromatographed on silica gel by eluting with 30% EtOAc/hexane to give 12.8 g (72%) of (2S,5fl)-4-(3-chloro-propyl)- 2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester as a light yellow oil. 1H NMR (300 MHz, CDCI3): delta 4.22 (m, 1 H), 3.64 (m, 3H), 3.23 (dd, J = 11.4, 3.9 Hz, 1 H), 2.55 (m, 1 H), 2.42 (m, 1 H), 2.22 (d, J = 11.4 Hz, 1 H), 1.87 (t, J = 6.3 Hz, 2H), 1.46 (s, 9H)7 1.21 (d, J = 6.9 Hz, 3H), 0.92 (d, J = 6.6 Hz, 3H).

The synthetic route of 1-Chloro-3-iodopropane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2006/44293; (2006); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com