Diethyl Ether → HCID 68420583, compound

HRID 900053Notes

Reaction equation

HRID 900053 reaction equation
Cl[C:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]=1.[Br:9][C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=1[C:12]([NH:14][NH2:15])=[O:13].[OH-].[Na+].C(OCC)C>C1C=CC=CC=1>[N:8]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]=1[NH:15][NH:14][C:12](=[O:13])[C:11]1[CH:16]=[CH:17][CH:18]=[CH:19][C:10]=1[Br:9]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 1014602-BromobenzohydrazideHCID 124293887-Chloro-3,4,5,6-tetrahydro-2H-azepine

Product 1

HCID 68420583HCID 68420583, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 7-chloro-3,4,5,6-tetrahydro-2H-azepine (1.32 g, 10 mmol, J. Med. Chem. 30, 1543-49) in benzene (20 ml) was added 2-bromo-benzoic acid hydrazide (1.08 g, 5 mmol) and the mixture was stirred at reflux temperature for 5 hrs. To the cooled reaction mixture was added 10% sodium hydroxide (10 ml) and diethyl ether (20 ml). The mixture was stirred for 30 min., the precipitate filtered off and dried in vacuo at 50° C. for 1 hr. affording 0.6 g of 2-bromo-benzoic acid-N′-(4,5,6,7-tetrahydro-3H-azepin-2-yl)-hydrazide which was dissolved in ethanol (20 ml) followed by addition of TEA (5 ml) and refluxed for 16 hrs. The volatiles were evaporated in vacuo and to the residue was added diethyl ether (10 ml) and ethyl acetate (5 ml). The precipitate was filtered off and dried in vacuo at 50° C. for 1 hr affording 0.35 g (24%) of the title compound as a solid.

Workup

  1. temperatureat reflux temperature for 5 hrs
  2. customTo the cooled reaction mixture
  3. stirringThe mixture was stirred for 30 min.
  4. filtrationthe precipitate filtered off
  5. customdried in vacuo at 50° C. for 1 hr

Sources & evidence

ORD record
ord-05c03c66ba394f8089db9d5a71c81778
Source dataset
uspto-grants-2008_04
Patent number
US07358238B2

Reaction notes

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