Ammonium Chloride → HCID 14181391, compound

HRID 2231827Notes

Reaction equation

HRID 2231827 reaction equation
Br[CH2:2][CH2:3][CH:4]([O:6][CH3:7])[CH3:5].[Mg].[Cl:9][C:10]1[C:11]2[C:12](=[O:23])[C:13]3[N:14]([CH2:19][CH2:20][CH2:21][N:22]=3)[C:15]=2[CH:16]=[CH:17][CH:18]=1.[Cl-].[NH4+]>CCOCC.ClCCCl>[Cl:9][C:10]1[C:11]2[C:12]([OH:23])([CH2:2][CH2:3][CH:4]([O:6][CH3:7])[CH3:5])[C:13]3[N:14]([CH2:19][CH2:20][CH2:21][N:22]=3)[C:15]=2[CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 132158761-Bromo-3-methoxybutaneHCID 14181389HCID 14181389, compound

Product 1

HCID 14181391HCID 14181391, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 1-bromo-3-methoxybutane (6.0 g) in dry ether (20 ml) was added dropwise under a nitrogen atmosphere to magnesium turnings (0.9 g) at such a rate as to maintain gentle reflux. After stirring at reflux for 0.5 hour the reaction mixture was chilled in ice and a solution of 9-chloro-3,4-dihydropyrimido[1,2-a]indol-10(2H)-one (3.5 g) in dry 1,2-dichloroethane (100 ml) was added dropwise. After stirring the reaction mixture for one hour at room temperature it was cooled and excess saturated ammonium chloride solution was added dropwise. The organic phase was separated and the aqueous phase was extracted with chloroform. The extracts were combined with the organic phase, dried (MgSO4) and the solution evaporated under reduced pressure to leave an oil which was triturated with ether to give a solid. Recrystallisation from ethyl acetate gave the title compound as colourless needles m.p. 164°-5°. Treatment of a solution of these needles in methanol with ethereal hydrogen chloride, followed by evaporation in vacuo gave a solid which was recrystallised from propan-2-ol to give the title compound as the hydrochloride, colourless crystals (2.81 g) m.p. 264°-5°.

Workup

  1. temperatureto maintain gentle reflux
  2. temperatureat reflux for 0.5 hour the reaction mixture
  3. temperaturewas chilled in ice
  4. stirringAfter stirring the reaction mixture for one hour at room temperature it
  5. temperaturewas cooled
  6. customThe organic phase was separated
  7. extractionthe aqueous phase was extracted with chloroform
  8. dry with materialdried (MgSO4)
  9. customthe solution evaporated under reduced pressure
  10. customto leave an oil which
  11. customwas triturated with ether
  12. customto give a solid
  13. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-d4013ca234684a719684a2c2fc2c38fb
Source dataset
uspto-grants-1988_11
Patent number
US04784996

Reaction notes

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