Sodium Bicarbonate → HCID 178495018, compound

HRID 353108Notes

Reaction equation

HRID 353108 reaction equation
[CH3:1][CH:2]1[C:7]([CH3:19])([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[N:15]=[N:16][NH:17][CH:18]=3)[CH:9]=2)[CH2:6][CH2:5][NH:4][CH2:3]1.C(=O)([O-])O.[Na+].I[CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH3:31]>CN(C)C=O>[NH3:4].[CH3:31][O:30][CH2:29][CH2:28][CH2:27][CH2:26][N:4]1[CH2:5][CH2:6][C:7]([CH3:19])([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[N:15]=[N:16][NH:17][CH:18]=3)[CH:9]=2)[CH:2]([CH3:1])[CH2:3]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 227078941-Iodo-4-methoxybutaneHCID 178430465HCID 178430465, compound

Product 2

HCID 222AmmoniaHCID 178495018HCID 178495018, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,4-dimethyl-4-(3-(1H-1,2,3-triazol-4-yl)phenyl)piperidine (Preparation 44, 50 mg, 0.19 mmol) in N,N-dimethylformamide (2 mL) was added sodium hydrogencarbonate (25 mg, 0.29 mmol) and 1-iodo-4-methoxybutane (Preparation 15, 50 mg, 0.23 mmol). The resultant mixture was heated at 60° C. overnight and then cooled to room temperature. The residue given was partitioned between saturated aqueous sodium hydrogencarbonate solution (25 mL) and ether (15 mL). The phases were separated and the aqueous layer was further extracted with ether (2×15 mL). The combined extracts were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by chromatography eluting with a gradient of CH2Cl2:MeOH:0.88 ammonia (100:8:1) to give the title compound as a colourless oil (15 mg, 22%).

Workup

  1. customThe residue given was partitioned between saturated aqueous sodium hydrogencarbonate solution (25 mL) and ether (15 mL)
  2. customThe phases were separated
  3. extractionthe aqueous layer was further extracted with ether (2×15 mL)
  4. dry with materialThe combined extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography
  8. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-cdf7315d71934b6c998780687d2da471
Source dataset
uspto-grants-2004_06
Patent number
US06750231B2

Reaction notes

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