Ammonium Chloride → HCID 14181390, compound

HRID 2231825Notes

Reaction equation

HRID 2231825 reaction equation
Br[CH2:2][CH2:3][CH:4]([O:6][CH3:7])[CH3:5].[Mg].[Cl:9][C:10]1[CH:11]=[CH:12][C:13]2[C:14](=[O:23])[C:15]3[N:16]([CH2:19][CH2:20][CH2:21][N:22]=3)[C:17]=2[CH:18]=1.[Cl-].[NH4+]>CCOCC.ClCCCl>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]2[C:14]([OH:23])([CH2:2][CH2:3][CH:4]([O:6][CH3:7])[CH3:5])[C:15]3[N:16]([CH2:19][CH2:20][CH2:21][N:22]=3)[C:17]=2[CH:18]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 132158761-Bromo-3-methoxybutaneHCID 14181388HCID 14181388, compound

Product 1

HCID 14181390HCID 14181390, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 1-bromo-3-methoxybutane (2.0 g) in dry ether (20 ml) was added dropwise under a nitrogen atmosphere to magnesium turnings (0.3 g) at such a rate as to maintain gentle reflux. After 0.5 hour the reaction mixture was cooled and a solution of 7-chloro-3,4-dihydropyrimido[1,2-a]indol-10(2H)-one (1.0 g) in dry 1,2-dichloroethane (50 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 in vacuo to leave an oil which was triturated with ether to give a solid. Recrystallisation from ethyl acetate gave the title compound as crystals m.p. 146.5°-148°. A solution of these crystals in warm propan-2-ol was treated with ethereal hydrogen chloride. Evaporation in vacuo followed by recrystallisation from propan-2-ol gave the title compound as the hydrochloride, colourless needles, m.p. 226°-8°.

Workup

  1. temperatureto maintain gentle reflux
  2. temperatureAfter 0.5 hour the reaction mixture was cooled
  3. temperaturewas cooled
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted with chloroform
  6. dry with materialdried (MgSO4)
  7. customthe solution evaporated in vacuo
  8. customto leave an oil which
  9. customwas triturated with ether
  10. customto give a solid
  11. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-4a45fbc9a50f4d77b628ec35e53d46ec
Source dataset
uspto-grants-1988_11
Patent number
US04784996

Reaction notes

Loading…