Sodium Bicarbonate → HCID 59423810, compound

HRID 501719Notes

Reaction equation

HRID 501719 reaction equation
[CH2:1]([C:6]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:7]=1[CH:8]=O)[CH2:2][CH2:3][CH:4]=[CH2:5].C([O-])(=O)C.[NH4+].C([BH3-])#[N:24].[Na+].C(=O)(O)[O-].[Na+]>CO>[CH2:1]([C:6]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:7]=1[CH2:8][NH2:24])[CH2:2][CH2:3][CH:4]=[CH2:5]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 86622343HCID 86622343, compound

Product 1

HCID 59423810HCID 59423810, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Step AJ (3): 2-(Pent-4-enyl)-5-(trifluoromethyl)benzaldehyde (200 mg, 0.83 mmol) and ammonium acetate (9.6 g, 124 mmol) was dissolved in methanol (35 mL). Sodium cyanoborohydride (311 mg, 4.95 mmol) was added. The reaction mixture was stirred at 65° C. in a high-pressure vessel for 2 h. Aqueous sodium bicarbonate solution was added and the reaction mixture was extracted with DCM. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by reverse phase chromatography to give (2-(pent-4-enyl)-5-(trifluoromethyl)phenyl)methanamine (65 mg, 32%) as a colorless oil. LC-MS (M+H)+=244.21.

Workup

  1. extractionthe reaction mixture was extracted with DCM
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-005488048b9d4bfaa69bc08fad3d822c
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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