Benzenemethanamine, 3,4-dichloro- → HCID 58928290, compound

HRID 852192Notes

Reaction equation

HRID 852192 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][C@H:17]4[CH2:19][O:18]4)=[CH:11][CH:10]=3)=[N:7][O:8][C:4]=2[CH:3]=1.[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:26][NH2:27]>C(O)C>[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:26][NH:27][CH2:19][C@@H:17]([OH:18])[CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([C:6]2[C:5]3[CH:20]=[CH:21][C:2]([F:1])=[CH:3][C:4]=3[O:8][N:7]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 1608Benzenemethanamine, 3,4-dichloro-HCID 58928269(R)-6-fluoro-3-(4-oxiranylmethoxy-phenyl)-benzo[d]isoxazole

Product 1

HCID 58928290HCID 58928290, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine (R)-6-fluoro-3-(4-oxiranylmethoxy-phenyl)-benzo[d]isoxazole (29) (250 mg, 0.86 mmol), 3,4-dichlorobenzylamine (617 mg, 3.50 mmol), ethanol (4.0 ml) and heat (˜80° C.) for 16 hours. Cool reaction at 0° C. for 1 h. Collect the solid product and wash with cold ethanol several times. Dry the solid at (50° C./0.5 mm Hg) overnight to give 313 mg (77% yield) of the title compound. Purity by LC/MS=96%, [M+H]+=461.

Workup

  1. temperatureCool
  2. customreaction at 0° C. for 1 h
  3. customCollect the solid product
  4. washwash with cold ethanol several times
  5. customDry the solid at (50° C./0.5 mm Hg) overnight

Sources & evidence

ORD record
ord-611cb5257f7341acae5483ad991f22eb
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

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