Hydrazine hydrate (1:1) → HCID 17940755, compound

HRID 2251938Notes

Reaction equation

HRID 2251938 reaction equation
[C:1]1([CH:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][CH2:10][N:9]([CH2:18][CH2:19][CH2:20][CH2:21][N:22]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN>C(O)C>[C:1]1([CH:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][CH2:10][N:9]([CH2:18][CH2:19][CH2:20][CH2:21][NH2:22])[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 541071242-[4-(1-Phenyl-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-butyl]-isoindol-1,3-dione

Product 1

HCID 17940755HCID 17940755, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Batch size: 38.0 g (<89.5 mmol) 2-[4-(1-phenyl-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-butyl]-isoindol-1,3-dione and 8.7 ml (179 mmol) hydrazine hydrate in 200 ml ethanol. The reaction mixture is filtered and the filtrate is concentrated under vacuum. The residue is taken up in 400 ml dichloromethane and washed twice each with 50 ml 10% NaCH solution. The organic phase is dried over sodium sulfate and, subsequently, the solvent is removed under vacuum. The purification occurs chromatographically over silica gel with CHCl3/CH3OH/TEA (95/5/0 to 90/9/1): Yield 15.6 g (59%).

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated under vacuum
  3. washwashed twice each with 50 ml 10% NaCH solution
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customsubsequently, the solvent is removed under vacuum
  6. customThe purification

Sources & evidence

ORD record
ord-f605b674808e45a6a5fea1017422db50
Source dataset
uspto-grants-2008_01
Patent number
US07320993B1

Reaction notes

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