1-Amino-2-propanol → HCID 14544472, compound

HRID 2051305Notes

Reaction equation

HRID 2051305 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[NH2:23][CH2:24][CH:25]([OH:27])[CH3:26]>O1CCCC1>[OH:27][CH:25]([CH3:26])[CH2:24][NH:23][C:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:9]

Participants

6

Reactant 4

HCID 41-Amino-2-propanolHCID 938Nicotinic AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformate

Product 1

HCID 14544472HCID 14544472, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-4 °C

Procedure

To 4.29 g (0 039 mol) of nicotinic acid suspended in 120 mL of dry tetrahydrofuran, 4.04 g (0.039 mol) of freshly distilled triethylamine was added in one portion. The resultant clear solution was cooled to -4° C. in an ice bath under argon. Ethyl chloroformate (4.33 g, 0.039 mol) in 25 mL of tetrahydrofuran was added at such a rate that the temperature of the solution did not exceed 0° C. Then, 3 g (0.039 mol) of 1-amino-2-propanol were added directly to the cold reaction mixture. The reaction mixture was allowed to come to room temperature and stirred for 2 hours. The precipitate was removed by filtration and the filtrate was evaporated in vacuo. The oily residue was washed several times with anhydrous ether and allowed to stand. The title compound was obtained as a white, hygroscopic, low-melting, waxy solid melting at 40° C. (6.11 g, 85%) and having the formula ##STR114##

Workup

  1. customdid not exceed 0° C
  2. customto come to room temperature
  3. customThe precipitate was removed by filtration
  4. customthe filtrate was evaporated in vacuo
  5. washThe oily residue was washed several times with anhydrous ether

Sources & evidence

ORD record
ord-734ff5a0ad204f23b33e0c8e76ecc893
Source dataset
uspto-grants-1991_05
Patent number
US05017566

Reaction notes

Loading…