Dibutyltin oxide → HCID 178489644, compound

HRID 2085461Notes

Reaction equation

HRID 2085461 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn](=O)CCCC)CCC.C[Si]([N:44]=[N+:45]=[N-:46])(C)C>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)([C:22]2[CH:23]=[CH:24][C:25]([C:26]3[NH:46][N:45]=[N:44][N:27]=3)=[CH:28][CH:29]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 227299114-[1-Benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-benzonitrile

Product 1

HCID 178489644HCID 178489644, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-[1-Benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-benzonitrile (0.24 g, 0.63 mmol) in toluene (5 mL) were added dibutyltin oxide (0.025 g, 0.1 mmol) and trimethylsilyl azide (0.15 g, 1.26 mmol). The reaction mixture was heated for 60 hours. The mixture was then cooled to room temperature and concentrated under vacuum. The residue was dissolved in methanol (5 mL) and then concentrated. The residue was partitioned between saturated aqueous sodium bicarbonate solution (5 mL) and ethyl acetate. The aqueous layer was washed with ethyl acetate (3×10 mL). The combined extracts were dried (MgSO4) and concentrated. Purification by flash chromatography with CH2Cl2/MeOH (9:1) afforded 0.19 g (71% yield) of 1-Benzyl-4-(3-methoxy-phenyl)4-[4-(1H-tetrazol-5-yl)-phenyl]-piperidine. 1HNMR (400 MHz, CD3OD) δ 7.95 (d, 2H), 7.44-7.41 (comp, 7H), 7.23-7.18 (m, 1H), 6.90-6.77 (comp, 2H), 6.76 (d, 1H), 6.70 (d, 1H), 4.21 (s, 2H), 3.64 (s, 3H), 3.30-2.41 (comp, 8H); MS (M+1) 426.2.

Workup

  1. temperatureThe reaction mixture was heated for 60 hours
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in methanol (5 mL)
  4. concentrationconcentrated
  5. customThe residue was partitioned between saturated aqueous sodium bicarbonate solution (5 mL) and ethyl acetate
  6. washThe aqueous layer was washed with ethyl acetate (3×10 mL)
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. concentrationconcentrated
  9. customPurification by flash chromatography with CH2Cl2/MeOH (9:1)

Sources & evidence

ORD record
ord-254f62cad62d4b1ebae947fad282971e
Source dataset
uspto-grants-2004_04
Patent number
US06720336B2

Reaction notes

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