1-Phenethylamine, (+)- → HCID 54045234, compound

HRID 2185657Notes

Reaction equation

HRID 2185657 reaction equation
[C:1]1([C@H:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:11]1[C:20]2[C:15](=[CH:16][C:17]([F:24])=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=2)[N:14]=[CH:13][N:12]=1>O1CCOCC1.C(Cl)Cl>[C:1]1([C@H:7]([NH:9][C:11]2[C:20]3[C:15](=[CH:16][C:17]([F:24])=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=3)[N:14]=[CH:13][N:12]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 6431891-Phenethylamine, (+)-HCID 106093584-Chloro-7-fluoro-6-nitroquinazoline

Product 1

HCID 54045234HCID 54045234, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 74 ml of (R)-1-phenyl-ethylamine in 100 ml of dioxane is added dropwise to 108.8 g of 4-chloro-6-nitro-7-fluoro-quinazoline in 800 ml of methylene chloride while cooling with an ice bath. The reaction mixture is stirred overnight at ambient temperature. For working up it is extracted with water. The organic phase is dried over magnesium sulphate and evaporated down. The residue is purified by chromatography through a silica gel column with petroleum ether/ethyl acetate (1:1) as eluant.

Workup

  1. temperaturewhile cooling with an ice bath
  2. extractionis extracted with water
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. customevaporated down
  5. customThe residue is purified by chromatography through a silica gel column with petroleum ether/ethyl acetate (1:1) as eluant

Sources & evidence

ORD record
ord-93f7e5374ce6434dba84d00080883010
Source dataset
uspto-grants-2002_06
Patent number
US06403580B1

Reaction notes

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