Sodium Bicarbonate → HCID 178477723, compound

HRID 353109Notes

Reaction equation

HRID 353109 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][NH:28][S:29]([CH2:32][CH3:33])(=[O:31])=[O:30]>CN(C)C=O>[NH3:4].[CH2:32]([S:29]([NH: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)(=[O:31])=[O:30])[CH3:33]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 22707949N-(2-iodoethyl)-1-ethanesulfonamideHCID 178430465HCID 178430465, compound

Product 2

HCID 222AmmoniaHCID 178477723HCID 178477723, compoundYield 75.3%

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 N-(2-iodoethyl)-1-ethanesulfonamide (Preparation 24, 60 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 on silica gel eluting with a gradient of CH2Cl2:MeOH:0.88 ammonia (100:8:1) to give the title compound as a colourless oil (28 mg, 38%).

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 on silica gel eluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-58ebda0a8ea946d5892308024411f047
Source dataset
uspto-grants-2004_06
Patent number
US06750231B2

Reaction notes

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