Diethyl Ether → HCID 21132489, compound

HRID 1987231Notes

Reaction equation

HRID 1987231 reaction equation
NN.C1(=O)[N:7]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:19][C@H:18]3[C@H:13]([CH2:14][C:15]4[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=4[CH2:17]3)[CH2:12]2)C(=O)C2=CC=CC=C12.C(OCC)C>C(O)C>[NH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:19][C@H:18]2[C@H:13]([CH2:14][C:15]3[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=3[CH2:17]2)[CH2:12]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 9321HydrazineHCID 21132490HCID 21132490, compound

Product 1

HCID 21132489HCID 21132489, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine (9 mg, 0.28 mmol) was added to a solution of 2-(3-Phthalimido-n-prop-1-yl)-cis-2,3,3a,4,9,9a-hexahydro-1H-benz[f]isoindole (50 mg, 0.14 mmol) in 1 mL of ethanol, and the mixture was refluxed for 6 hours. The mixture was cooled to room temperature, and 5 mL of diethyl ether was added with stirring. After 30 minutes, a white solid had precipitated. The solid was collected by filtration, rinsed with diethyl ether, then stirred in 10 mL of chloroform. The solids were filtered and washed with chloroform. The filtrate was concentrated to yield 20 mg of a colorless oil as product. Yield=63%. NMR (300 MHz, CD3OD) δ 7.09-7.05 (m, 4H), 3.03-2.97 (m, 2H), 2.77-2.70 (dd, 2H, J=6 Hz, 14 Hz), 2.68-2.58 (m, 4H), 2.50-2.44 (dd, 2H, J=5 Hz, 14 Hz), 2.30 (t, 2H, J=7 Hz), 1.82 (t, 2H, J=7 Hz), 1.61 (tt, 2H, J=7 Hz, 8 Hz, 7 Hz).

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. customa white solid had precipitated
  3. filtrationThe solid was collected by filtration
  4. washrinsed with diethyl ether
  5. stirringstirred in 10 mL of chloroform
  6. filtrationThe solids were filtered
  7. washwashed with chloroform
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9da8a22b5cb64151a93fa0c437aa2b36
Source dataset
uspto-grants-2009_06
Patent number
US07550500B2

Reaction notes

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