Hydrazine → HCID 67386067, compound

HRID 905959Notes

Reaction equation

HRID 905959 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]1[CH2:9][CH2:8][CH2:7][C@H:6]([N:10]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:5]1.NN>CCO>[CH3:1][O:2][CH2:3][C@H:4]1[CH2:9][CH2:8][CH2:7][C@H:6]([NH2:10])[CH2:5]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 67386001HCID 67386001, compound

Product 1

HCID 67386067HCID 67386067, compoundYield 218.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Racemic trans-2-(3-methoxymethyl-cyclohexyl)-isoindole-1,3-dione (0.205 g, 0.75 mmol) was suspended in EtOH (5 mL) and hydrazine (0.07 mL, 2.25 mmol) was added. The resulting colorless mixture was stirred at 50° C. for 3 hours before cooled to RT. The solid that precipitated was filtered off and washed with EtOH. The filtrate was evaporated to give 0.235 g of racemic trans-3-methoxymethyl-cyclohexylamine as a white solid (50% pure by NMR).

Workup

  1. temperaturebefore cooled to RT
  2. customThe solid that precipitated
  3. filtrationwas filtered off
  4. washwashed with EtOH
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-098f876620d54e96b0ae3896ee4071ba
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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