Acetic Acid → 4-(Morpholinomethyl)aniline

HRID 857906Notes

Reaction equation

HRID 857906 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-])=O.C(O)(=O)C.[OH-].[Na+]>O.[Fe]>[N:9]1([CH2:8][C:7]2[CH:15]=[CH:16][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 7831834-(4-Nitrobenzyl)morpholine

Product 1

HCID 7768514-(Morpholinomethyl)anilineYield 85.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent2×

Procedure

A stirred suspension of 4-(4-nitrobenzyl)morpholine (500 mg) (prepared according to a modified procedure described by Leffler and Volwiler, JACS, 1938, 60, 896) in water (4.15 mL) was treated with glacial acetic acid (0.5 mL). The reaction mixture was heated to gentle reflux and then treated with iron powder (500 mg) over 10 minutes. After stirring at reflux for a further 10 minutes the reaction mixture was allowed to cool to room temperature. The reaction mixture was treated with water (10 mL) and then basified to pH 12 with a 4 M aqueous solution of sodium hydroxide. The aqueous was extracted three times with diethyl ether (1×40 mL, 2×10 mL). The combined organic extracts were dried over magnesium sulfate and then evaporated to give the title compound (370 mg) as a white solid, m.p. 96–97° C. MS: 193 [MH]+.

Workup

  1. customprepared
  2. temperatureThe reaction mixture was heated
  3. temperatureto gentle reflux
  4. temperatureat reflux for a further 10 minutes the reaction mixture
  5. extractionThe aqueous was extracted three times with diethyl ether (1×40 mL, 2×10 mL)
  6. dry with materialThe combined organic extracts were dried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-6cb692e2599e4f60994c5d792de1ae38
Source dataset
uspto-grants-2006_12
Patent number
US07148215B2

Reaction notes

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