Ammonia → 1,3-Dichloro-6,7,8,9,10,12-hexahydroazepino[2,1-b]quinazoline hydrochloride (1:1)

HRID 375611Notes

Reaction equation

HRID 375611 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4](=O)[N:5]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:6]1=[N:7]2.C(Cl)(Cl)Cl.CO.N>C([SiH](CC)CC)C.[Cl-].[Zn+2].[Cl-]>[ClH:1].[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[CH2:4][N:5]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:6]1=[N:7]2

Participants

7

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 6212ChloroformHCID 10039448HCID 10039448, compound

Product 1

HCID 189922831,3-Dichloro-6,7,8,9,10,12-hexahydroazepino[2,1-b]quinazoline hydrochloride (1:1)

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 12052TriethylsilaneSolvent3×

Procedure

To a solution of 1 g of 1,3-dichloro-7,8,9,10-tetrahydroazepino[2,1-b]quinazolin-12(6H)-one in 15 mL of triethylsilane was added 8 g of anhydrous zinc chloride and the mixture was refluxed under nitrogen with vigorous stirring. The triethylsilane was replenished in about 8-hour intervals. When the reaction was judged complete by TLC (300:25:1 chloroform:methanol: 28% aqueous ammonia, basified aliquot) the excess of triethylsilane and other volatiles were removed in vacuo and the residue was purified and worked-up as in Method A to give the desired 1,3-dichloro-6,7,8,9,10,12-hexahydroazepino[2,1-b]quinazoline hydrochloride as white crystalline solid.

Workup

  1. temperaturethe mixture was refluxed under nitrogen with vigorous stirring
  2. customwere removed in vacuo
  3. customthe residue was purified and worked-up as in Method A

Sources & evidence

ORD record
ord-7c94258826554197ba66b102f8e23eb6
Source dataset
uspto-grants-1996_01
Patent number
US05486512

Reaction notes

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