Diethyl Ether → 4-(3-Nitrobenzyl)morpholine
Reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[N+:7]([C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH2:13]Cl)([O-:9])=[O:8].C(OCC)C>C1(C)C=CC=CC=1>[N+:7]([C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH2:13][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)([O-:9])=[O:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
A solution of morpholine (4.57 mL) in toluene (10 mL) at 5° C. was treated with a solution of 3-nitrobenzyl chloride (4.29 g) in toluene (10 mL). After stirring at 85° C. for 2 hours the reaction mixture was allowed to cool to room temperature and then left to stand overnight. The reaction mixture was treated with diethyl ether (100 mL), then washed three times with water (50 mL), then three times with brine (50 mL), dried over magnesium sulfate and then evaporated. The residue was subjected to column chromatography on silica eluting with ethyl acetate to give the title compound (2.86 g) as a white solid, m.p. 48–50° C. 1H NMR [(CDCl3]: δ 8.24 (s, 1H), 8.13 (d, 1H), 7.70 (d, 1H), 7.50 (t, 1H), 3.74 (t, 4H), 3.60 (s, 2H) and 2.48 (s, 4H).
Workup
- temperatureto cool to room temperature
- waitleft
- waitto stand overnight
- washwashed three times with water (50 mL)
- dry with materialthree times with brine (50 mL), dried over magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-c5f2422f441f4ad08cec5868cff11d31
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07148215B2
Reaction notes
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