Hydrazine → 1-[[3-(3-Aminopropoxy)phenyl]carbonyl]piperidine

HRID 1731412Notes

Reaction equation

HRID 1731412 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]([CH:27]=[CH:28][CH:29]=1)[C:19]([N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:20].NN>C(O)C>[NH2:3][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]([C:19]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])[CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 137325571-[3-[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propoxy]benzoyl]piperidine

Product 1

HCID 137325581-[[3-(3-Aminopropoxy)phenyl]carbonyl]piperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a warm solution of 0.5 g. of 1-[3-[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propoxy]benzoyl]piperidine in 20 ml. of absolute ethanol is added 1 ml. of hydrazine. The mixture is stirred at room temperature for 1 hour and is filtered. The filtrate is allowed to stand at room temperature for 18 hours and again is filtered. The filtrate is evaporated in a rotary evaporator and the residue is partitioned between 50 ml. of ether and 50 ml. of water. The ether layer is dried over magnesium sulfate, is filtered and is evaporated to give 80 mg. of oil. The oil is purified by HPLC using 1-Silica Prep Pac (Waters) and a combination of methanol, ethyl acetate and 1% triethylamine to give the analytical sample.

Workup

  1. filtrationis filtered
  2. waitto stand at room temperature for 18 hours
  3. filtrationagain is filtered
  4. customThe filtrate is evaporated in a rotary evaporator
  5. customthe residue is partitioned between 50 ml
  6. dry with materialThe ether layer is dried over magnesium sulfate
  7. filtrationis filtered
  8. customis evaporated
  9. customto give 80 mg
  10. customThe oil is purified by HPLC
  11. customa combination of methanol, ethyl acetate and 1% triethylamine to give the analytical sample

Sources & evidence

ORD record
ord-0f6d5a9c9d604a8aacbafa64b7916564
Source dataset
uspto-grants-1986_11
Patent number
US04621142

Reaction notes

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