Sodium Bicarbonate → HCID 68541243, compound

HRID 1446722Notes

Reaction equation

HRID 1446722 reaction equation
C([NH:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=[C:11]([CH2:19][N:20]([CH3:22])[CH3:21])[N:10]=1)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>S(=O)(=O)(O)O>[C:15]([C:13]1[CH:12]=[C:11]([CH2:19][N:20]([CH3:22])[CH3:21])[N:10]=[C:9]([NH2:8])[CH:14]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 68541578HCID 68541578, compound

Product 1

HCID 68541243HCID 68541243, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Add concentrated sulfuric acid (20 mL) to benzyl-(4-tert-butyl-6-dimethylaminomethyl-pyridin-2-yl)-amine (0.88 g, 2.96 mmol) at ambient temperature and stir for 1.5 hours. Adjust the pH of the aqueous solution carefully with saturated sodium bicarbonate solution. Extract the aqueous phase with ethyl acetate (3×75 mL) and pool, desiccate, filter and concentrate to a residue. Dissolve the residue in methanol and subject the material to SCX chromatography. Concentrate the methanolic ammonia eluent and plug chromatograph the amine to provide the title compound (0.56 g, 2.7 mmol). MS(ES), m/z 208 (M+1).

Workup

  1. extractionExtract the aqueous phase with ethyl acetate (3×75 mL) and pool, desiccate
  2. filtrationfilter
  3. concentrationconcentrate to a residue
  4. dissolutionDissolve the residue in methanol
  5. concentrationConcentrate the methanolic ammonia eluent and plug chromatograph the amine

Sources & evidence

ORD record
ord-152ff3d30bac4e94a1e36bc3ab70e6d1
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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