Acetic Acid → 4-(Morpholinomethyl)aniline

HRID 2174218Notes

Reaction equation

HRID 2174218 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.C(O)(=O)C>[Zn].C(O)C>[O:14]1[CH2:13][CH2:12][N:11]([CH2:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 7831834-(4-Nitrobenzyl)morpholine

Product 1

HCID 7768514-(Morpholinomethyl)aniline

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

A solution of (i) (205 mg, 0.92 mmol) in 50:50 acetic acid:ethanol (10 mL) was treated with zinc dust (370 mg, 5.53 mmol) then stirred at RT under N2 for 4 hr. The mixture was concentrated under vacuum and the residue suspended in EtOAc (20 mL). The solution was filtered to remove undissolved zinc, and then washed with water (50 mL). The aqueous layer was neutralised then extracted with EtOAc (3×20 mL). The organic extracts were combined and concentrated to give (ii). Sample was used in subsequent reactions without further purification. 1H NMR (400 MHz, CDCl3) δ 8.20-8.15 (m, 2H), 7.55-7.50 (m, 2H), 3.76-3.70 (m, 4H), 3.59 (s, 2H), 2.49-2.42 (m, 4H).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. filtrationThe solution was filtered
  3. customto remove undissolved zinc
  4. washwashed with water (50 mL)
  5. extractionThe aqueous layer was neutralised then extracted with EtOAc (3×20 mL)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-93027b7725a545739f25963588431409
Source dataset
uspto-grants-2015_06
Patent number
US09060515B2

Reaction notes

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