Hydrazine hydrate (1:1) → HCID 19081204, compound

HRID 963486Notes

Reaction equation

HRID 963486 reaction equation
[CH:1]1([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[C:10](=[O:25])[CH:9]([N:26]3C(=O)C4=CC=CC=C4C3=O)[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.NN>O1CCCC1>[NH2:26][CH:9]1[N:8]=[C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[C:10]1=[O:25]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19081279HCID 19081279, compound

Product 1

HCID 19081204HCID 19081204, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of (3RS)-5-cyclohexyl-2,3-dihydro-3-phthalimido-1-(pyridin-2-yl)methyl-1H-1,4-benzodiazepin-2-one (0.22 g) in tetrahydrofuran (10 ml) was treated with a solution of hydrazine monohydrate (23 mg) in tetrahydrofuran (1 ml) at ambient temperature, and the mixture was stirred for 2 hours at the same temperature, then heated at reflux temperature for 1 hour. After cooling, the resultant precipitates were filtered off. The filtrate was concentrated in vacuo. The residue was taken up with 1N aqueous hydrohloric acid and washed with isopropyl ether. The aqueous layer was alkalined with sodium carbonate and extracted with chloroform. The extract was dried over sodium sulfate, filtered and concentrated in vacuo to give (3RS)-3-amino-5-cyclohexyl-2,3-dihydro-1-(pyridin-2-yl)methyl-1H-1,4-benzodiazepin-2-one (0.12 g) as an yellow oil which was used in a following reaction step without further purification.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 1 hour
  3. temperatureAfter cooling
  4. customthe resultant precipitates
  5. filtrationwere filtered off
  6. concentrationThe filtrate was concentrated in vacuo
  7. washwashed with isopropyl ether
  8. extractionextracted with chloroform
  9. dry with materialThe extract was dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e69e5e45209438b89ea7d97810221dc
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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