Hydrochloric Acid → 4-(3-Chloropropyl)morpholinium chloride
Reaction equation
Br[CH2:2][CH2:3][CH2:4][Cl:5].[NH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.Cl>C1(C)C=CC=CC=1>[ClH:5].[Cl:5][CH2:4][CH2:3][CH2:2][N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 84 °C
Procedure
To a solution of 1-bromo-3-chloropropane (45 g, 0.29 mol) in toluene (100 mL) was added morpholine (38 g, 0.44 mol). The solution was stirred at 84° C. for 3 h, during which time a precipitate formed. After cooling to rt, the precipitate was isolated by vacuum filtration, washed with ether, and the solid was discarded. The mother liquor was acidified with HCl (4 M in dioxane, 72 mL, 0.29 mol), which caused the desired product to precipitate as an HCl salt. Solvent was removed under reduced pressure, and the resultant solid was dried to afford the title compound (53 g, 90%): 1H NMR (DMSO-d6) δ: 11.45 (1H, br s), 3.94-3.77 (4H, m), 3.74 (2H, t), 3.39 (2H, m), 3.15 (2H, m), 3.03 (2H, m), 2.21 (2H, m).
Workup
- customformed
- temperatureAfter cooling to rt
- customthe precipitate was isolated by vacuum filtration
- washwashed with ether
Sources & evidence
- ORD record
- ord-66a521990be04b45a6bac3a6d2def200
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895549B2
Reaction notes
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