Hydrazine hydrate (1:1) → HCID 86749781, compound

HRID 741552Notes

Reaction equation

HRID 741552 reaction equation
[O:1]1[N:5]2[C:6]3[CH:18]=[CH:17][CH:16]=[CH:15][C:7]=3[CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C@@H:4]2[CH2:3][C@H:2]1[CH2:19][N:20]1C(=O)C2C(=CC=CC=2)C1=O.O.NN>C(O)C>[O:1]1[N:5]2[C:6]3[CH:18]=[CH:17][CH:16]=[CH:15][C:7]=3[CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C@@H:4]2[CH2:3][C@H:2]1[CH2:19][NH2:20]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86749782HCID 86749782, compound

Product 1

HCID 86749781HCID 86749781, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (±)-cis-2-[(2,3,3a,8-tetrahydrodibenz[c,f]isoxazolo[2,3-a]azepin-2-yl)methyl]-1H-isoindole-1,3(2H)-dione (4 g), prepared following the procedure of example 1, and hydrazine hydrate (0.5 ml) in ethanol (80 ml) was stirred at 80° C. for 4 hours. The precipitate was filtered off and purified by open column chromatography over silica gel (eluent: CH2Cl2 /2-propanone 8/2). The pure fractions were collected and evaporated. The residue (1.6 g) was convened into the oxalic acid salt (1:1) in C2H5OH at room temperature. The residue (0.8 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 97.5/2.5 to 95/5). The pure fractions were collected and evaporated, yielding 0.6 g (22%) of (±)-cis-2,3,3a,8-tetrahydrodibenz[c,f]isoxazolo-[2,3-a]azepine-2-methanamine (comp. 9).

Workup

  1. customprepared
  2. filtrationThe precipitate was filtered off
  3. custompurified by open column chromatography over silica gel (eluent: CH2Cl2 /2-propanone 8/2)
  4. customThe pure fractions were collected
  5. customevaporated
  6. customwas convened into the oxalic acid salt (1:1) in C2H5OH at room temperature
  7. customThe residue (0.8 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 97.5/2.5 to 95/5)
  8. customThe pure fractions were collected
  9. customevaporated

Sources & evidence

ORD record
ord-385f13f7edbc46e9bd60f598862326b2
Source dataset
uspto-grants-1996_09
Patent number
US05552399

Reaction notes

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