Hydrazine hydrate (1:1) → 4-[2-(Morpholin-4-yl)ethoxy]phenol

HRID 2097360Notes

Reaction equation

HRID 2097360 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:33]=[CH:32][C:13]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]C34C=CC=CC3C(NC4=O)=O)=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.O.[NH2:35]N>CCO>[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:33]=[CH:32][C:13]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH2:35])=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:33]=[CH:32][C:13]([OH:14])=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 231324272-[6-(4-(2-Morpholin-4-yl-ethoxy)-phenoxy)-hexyl]-phthalimide

Product 2

HCID 231324384-[2-(Morpholin-4-yl)ethoxy]phenolHCID 231324536-[4-(2-Morpholin-4-yl-ethoxy)-phenoxy]-hexylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[6-(4-(2-Morpholin-4-yl-ethoxy)-phenoxy)-hexyl]-phthalimide (5.46 g crude mixture from above, ≈9.67 mmol) and hydrazine hydrate (3.66 ml, 60 mmol) were dissolved in EtOH (80 mL) and stirred under reflux for 17 h. The precipitate was filtered off and washed with EtOH (1×50 mL). The filtrate was concentrated under reduced pressure, the residue was suspended in THF (20 mL) and the precipitate was filtered off, washed with THF (2×5 mL) and the filtrate was concentrated under reduced pressure to give the title compound together with some 4-(2-morpholin-4-yl-ethoxy)-phenol (≈2:1).

Workup

  1. temperatureunder reflux for 17 h
  2. filtrationThe precipitate was filtered off
  3. washwashed with EtOH (1×50 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. filtrationthe precipitate was filtered off
  6. washwashed with THF (2×5 mL)
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e3bf2599969844498b38163b77316c8b
Source dataset
uspto-grants-2013_05
Patent number
US08450348B2

Reaction notes

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