HCID 12287603, compound → 4,5-dihydro-4-(4-chlorophenyl)-2-(isopropyl)-3H-1,3,4-benzotriazepine hydrochloride

HRID 1979684Notes

Reaction equation

HRID 1979684 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[NH2:10].[C:18](OCC)(OCC)(OCC)[CH:19]([CH3:21])[CH3:20]>C(#N)C.Cl.CCOCC>[ClH:17].[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([N:9]2[CH2:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=[C:18]([CH:19]([CH3:21])[CH3:20])[NH:10]2)=[CH:12][CH:13]=1

Participants

6

Reactant 2

HCID 12287603HCID 12287603, compoundHCID 133765451-[(2-Aminophenyl)methyl]-1-(4-chlorophenyl)hydrazine

Product 1

HCID 133765634,5-dihydro-4-(4-chlorophenyl)-2-(isopropyl)-3H-1,3,4-benzotriazepine hydrochlorideYield 122.8%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture of 3 g (0.012 m) of 1-[(2-aminophenyl)methyl]-1-(4-chlorophenyl)hydrazine of Example 12b and 3.56 g (0.024 m) of triethyl orthoisobutyrate in 50 ml of acetonitrile, sufficient ethereal HCl was added to make the mixture acidic. The mixture was refluxed overnight (about 16 hours), cooled and the product filtered off as the hydrochloride salt. Recrystallization by suspending the product in ethanol, adding sufficient methanol to afford a solution and diluting with anhydrous ether gave 2.5 g (62%) of 4,5-dihydro-4-(4-chlorophenyl)-2-(isopropyl)-3H-1,3,4-benzotriazepine hydrochloride, m.p. 255°-258° C.

Workup

  1. additionwas added
  2. temperatureThe mixture was refluxed overnight (about 16 hours)
  3. temperaturecooled
  4. filtrationthe product filtered off as the hydrochloride salt
  5. customRecrystallization
  6. additionadding sufficient methanol
  7. customto afford a solution

Sources & evidence

ORD record
ord-f0dc7745488f472ca6124f5e1482a064
Source dataset
uspto-grants-1984_11
Patent number
US04482547

Reaction notes

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