Hydrazine → HCID 69216118, compound

HRID 747839Notes

Reaction equation

HRID 747839 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:11]23[CH2:30][CH:15]([CH2:16][CH:17]([N:19]4C(=O)C5C(=CC=CC=5)C4=O)[CH2:18]2)[N:14]([CH2:31][CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:13][CH:12]3[CH3:40])[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].NN>C(O)C>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:11]23[CH2:30][CH:15]([CH2:16][CH:17]([NH2:19])[CH2:18]2)[N:14]([CH2:31][CH2:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:13][CH:12]3[CH3:40])[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 69216108HCID 69216108, compound

Product 1

HCID 69216118HCID 69216118, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[5-(3-Isopropoxy-phenyl)-4-methyl-2-(3-phenyl-propyl)-2-aza-bicyclo[3.3.1]non-7-yl]-isoindole-1,3-dione (3.16 g, 7.8 mmol) and hydrazine (1.4 g, 43,7 mmol) were dissolved in ethanol (150 ml) and refluxed overnight. The solution was then cooled and the white percipitate was filtered and washed with cold ethanol. The solution was concentrated in vacuu and the crude material taken up in 3;1 CH2Cl2:THF. The resulting white percipitate was filtered and washed with cold CH2Cl2. The organic layer was concentrated to yield 3.07 g (97%) of the desired product as a yellow soild. 1H NMR (CDCl3) 7.18 (m, 6H), 6.71 (m, 3H), 4.56 (sept., J=6, 1H), 3.51 (m, 1H), 3.19 (br, 1H), 2.82 (m, 1H), 2.66 (m, 3H), 2.50 (m, 2H), 2.34 (m, 3H), 2.11 (m, 1H), 1.82 (m, 2H), 1.80 (m, 1H), 1.29 (d, J=6 Hz, 6H), 0.90 (m, 2H), 0.71 (d, J=7.2, 3H).

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe solution was then cooled
  3. filtrationthe white percipitate was filtered
  4. washwashed with cold ethanol
  5. concentrationThe solution was concentrated in vacuu
  6. filtrationThe resulting white percipitate was filtered
  7. washwashed with cold CH2Cl2
  8. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-c73376267ccb4ed2b4e52fb2d457afd8
Source dataset
uspto-grants-2008_07
Patent number
US07399762B2

Reaction notes

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