HCID 23440726, compound → HCID 23440716, compound

HRID 2119485Notes

Reaction equation

HRID 2119485 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:14]=3)[CH:9]2[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-])=O)=[CH:29][CH:28]=2)=[CH:4][CH:3]=1.Cl[Sn]Cl.O>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:14]=3)[CH:9]2[CH2:26][C:27]2[CH:28]=[CH:29][C:30]([NH2:33])=[CH:31][CH:32]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 23440726HCID 23440726, compoundHCID 43835034Tin dichloride dihydrate

Product 1

HCID 23440716HCID 23440716, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(4-fluorophenyl)-6-phenylmethoxy-1-{4-nitrobenzyl}-1,2,3,4-tetrahydroisoquinoline (3 g, 6.4 mmol) and SnCl2.H2O (7.2 g, 32 mmol) in DMF was stirred at room temperature overnight. The solvent was removed and the residue was treated with ethyl acetate (200 ml) and water (200 ml). The organic layer was dried over MgSO4, filtered and concentrated to provide the title compound (2.8 g, 100% yield): ES−MS (m/z) 439 [M+H]+.

Workup

  1. customThe solvent was removed
  2. additionthe residue was treated with ethyl acetate (200 ml) and water (200 ml)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c07f199665724d0fa8b1bf853361a552
Source dataset
uspto-grants-2004_02
Patent number
US06686351B2

Reaction notes

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