Hydrazine hydrate (1:1) → 6-[4-(Morpholinomethyl)phenoxy]hexylamine

HRID 2097370Notes

Reaction equation

HRID 2097370 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:31]=[CH:30][C:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]3C(=O)C4=CC=CC=C4C3=O)=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.O.NN>C(O)C.C1COCC1>[O:1]1[CH2:2][CH2:3][N:4]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])=[CH:30][CH:31]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 23132451N-(6-[4-(Morpholinomethyl)phenoxy]hexyl)phthalimide

Product 1

HCID 231324366-[4-(Morpholinomethyl)phenoxy]hexylamine

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of N-(6-[4-(morpholinomethyl)phenoxy]hexyl)phthalimide (1.66 g, 3.94 mmol) in 1:1 ethanol/THF (28 mL) under nitrogen atmosphere was added hydrazine hydrate (1.4 mL, 29 mmol). The reaction was heated to reflux overnight, then cooled and concentrated. THF was added (30 mL) and the mixture sonicated for 30 min, followed by filtration. The filtrate was concentrated, redissolved in 10 mL THF, and dried with Na2SO4. Concentration gave the title compound.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. temperaturecooled
  4. concentrationconcentrated
  5. additionTHF was added (30 mL)
  6. customthe mixture sonicated for 30 min
  7. filtrationfollowed by filtration
  8. concentrationThe filtrate was concentrated
  9. dissolutionredissolved in 10 mL THF
  10. dry with materialdried with Na2SO4
  11. concentrationConcentration

Sources & evidence

ORD record
ord-f1a437eafaf748ab928239538c06970e
Source dataset
uspto-grants-2013_05
Patent number
US08450348B2

Reaction notes

Loading…