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

HRID 1023289Notes

Reaction equation

HRID 1023289 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-phenylethylamine in 100 ml of dioxane is dropped into 108.8 g of 4-chloro-6-nitro-7-fluoro-quinazoline in 800 ml of methylene chloride with cooling. The reaction mixture is washed with water after stirring overnight at room temperature, the organic phase is separated, dried and evaporated. The obtained residue is purified by chromatography over a silica gel column (petroleum ether/ethyl acetate=1:1). Yield: 52.9 g (35% of theory); melting point: 203° C.; mass spectrum (ESI+): m/z=313 [M+H]+.

Workup

  1. temperaturewith cooling
  2. washThe reaction mixture is washed with water
  3. customthe organic phase is separated
  4. customdried
  5. customevaporated
  6. customThe obtained residue is purified by chromatography over a silica gel column (petroleum ether/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-698c895cf4ef4bb895f025ca1ca11adc
Source dataset
uspto-grants-2014_05
Patent number
US08722694B2

Reaction notes

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