Ammonium Chloride → 4-(Morpholinomethyl)aniline

HRID 2247252Notes

Reaction equation

HRID 2247252 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:6][CH:5]=1)([O-])=O.[NH4+].[Cl-]>CCO.O.[Fe]>[N:11]1([CH2:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 7831834-(4-Nitrobenzyl)morpholine

Product 1

HCID 7768514-(Morpholinomethyl)aniline

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-[(4-nitrophenyl)methyl]morpholine (220 mg, 1.0 mmol, Step A), iron powder (279 mg, 5.0 mmol) and NH4Cl (39 mg, 0.7 mmol) in EtOH (3 mL) and H2O (3 mL) was stirred for 4 h at 80° C. Filtration and concentration gave the crude 4-(morpholin-4-ylmethyl)-phenylamine, which was used in next step without further purification.

Workup

  1. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-ed20f61883ad4d4ea740962a38a92c46
Source dataset
uspto-grants-2010_03
Patent number
US07687643B2

Reaction notes

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