Serinol

2-amino-1, 3-propanediol, which carries the trivial name of serinol, is an organic compound from the group of alkanolamines.The name serinol was chosen because of the structural similarity to the amino acidserine. In extension, derivatives thereof with substituents on the carbons of serinol are also called serinols.Under standard conditions, it is a solid, which is very soluble in water. 2-amino-1, 3-propanediol is a very stable, hygroscopic and corrosive substance. white to off-white adhering

In an autoclave, a mixture of Raney nickel (4 g, wet) and ammonium hydroxide solution (257 g, 28percent NH3 in water, 4.2 mol) was heated to 65° C. under 250 psi of hydrogen atmosphere. A solution of 1, 3-dihydroxyacetone (38 g, 0.42 mol) in methanol (76 ml) was pumped into the autoclave over a period of 3 h. After the addition was complete, the reaction mixture was maintained at 65° C. and 250 psi hydrogen pressure for additional 3 h. The autoclave was then cooled to ambient temperature and depressurized. The resulting reaction mixture was filtered to remove the catalyst. Ammonia and most of the water were removed by distillation under reduced pressure. GC analysis of the crude product showed a mixture of 91percent serinol (2-amino-1, 3-propanediol) and 7percent bis-adduct (2, 2′-iminobis-1, 3-propanediol). (0025) An aqueous solution of the crude product mixture was loaded to a column of Amberlyst® 15 and eluted with water until neutral pH. GC analysis of the water eluate showed mainly the bis-adduct and other unidentified impurities. The column was then eluted with 300 ml of 4M ammonium hydroxide solution to recover the serinol. The eluate was then stripped under vacuum to remove ammonia and water. The residue was triturated with a 1:1 mixture of 2-butanol and 2-methyltetrahydrofuran to yield crystalline serinol (27 g, 71percent yield). Assay by GC: 97percent; Assay by titration: 101percentIn an autoclave, ammonia gas (13 g, 0.77 mol) was charged to a suspension of Raney nickel (4 g, wet) in methanol (100 ml) and then heated to 65° C. under 250 psi of hydrogen atmosphere. A solution of 1, 3-dihydroxyacetone (58percent solution in water, 200 g, 1.29 mol) was pumped into the autoclave over a period of 2 h. After the addition was complete, the reaction mixture was continued to hydrogenate at 65° C. temperature and 250 psi hydrogen pressure for an additional 3 h. The autoclave was cooled to ambient temperature and depressurized. The reaction mixture was filtered to remove the catalyst and evaporated under vacuum to remove ammonia and most of the water. The crude product was shown to contain 2.4percent serinol and 90percent 2, 2′-iminobis-1, 3-propanediol by GC analysis. (0029) An aqueous solution of the crude product was loaded to a column of Amberlyst® 15 and eluted with water until neutral pH. GC analysis of the water eluate showed complete removal of serinol (FIG. 5). The water eluate was then evaporated under vacuum, the residue was dissolved in 1:1 mixture of 2-butanol and tetrahydrofuran, treated with activated carbon, and concentrated to yield the bis-adduct 2, 2′-iminobis-1, 3-propanediol as a viscous oil (65 g, 61percent). Assay by GC: 99percent20percent 2-nitro 1, 3-propanediol methanol solution 1250g added 5percent palladium / carbon 3.5g, continuous hydrogen gas 70L, hydrogen pressure 3MPa, 75 ° C for 5 hours to obtain a serinol solution.Palladium/charcoal was filtered off, washed and reused.Step 4: Distill high purity serinol in high vacuumThe serinol solution is pumped into a high-vacuum distillation vessel, evacuated to 40 Pa, and the methanol is distilled and reused.The yield of serinol was 97.2percent.U. Synthesis of Serinol (Compound 21)To a stirred solution of Compound 20 (1 g., 0.0062 mol) in methanol (10 mL) amberlyte resin (0.2 g.) was added and stirred at room temperature for 12 h. The reaction mixture was filtered and organic layer was concentrated but the compound was bound with the acidic resin, so the resin in methanol was basified by passing NH

It is the main raw material for the synthetic drug iopamidol

Molecular Weight:91.11
XLogP3:-2
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:91.063328530
Monoisotopic Mass:91.063328530
Topological Polar Surface Area:66.5
Heavy Atom Count:6
Complexity:28
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes