Acetic Acid → HCID 18975558, compound

HRID 2393296Notes

Reaction equation

HRID 2393296 reaction equation
[CH2:1]([NH:6][C:7](=O)[CH2:8][C:9]1[CH:14]=[C:13]([C:15]2[NH:16][CH:17]=[CH:18][N:19]=2)[CH:12]=[C:11]2[O:20][CH2:21][O:22][C:10]=12)[CH2:2][CH2:3][CH2:4][CH3:5].C(O)(=O)C.[BH4-].[Na+].Cl>O1CCCC1.O>[CH2:1]([NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([C:15]2[NH:16][CH:17]=[CH:18][N:19]=2)[CH:12]=[C:11]2[O:20][CH2:21][O:22][C:10]=12)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 67662805HCID 67662805, compound

Product 1

HCID 18975558HCID 18975558, compoundYield 74.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-pentyl-(5-imidazolyl-2,3-methylenedioxyphenyl) acetamide (2.13 g, 6.75 mmol) and acetic acid (3.5 ml, 61.1 mmol) in tetrahydrofuran (80 ml) was added dropwise to a mixture of sodium borohydride (2.34 g, 61.9 mmol) and tetrahydrofuran (25 ml) over 20 minutes under reflux, and then stirring was continued for 2 hours under reflux. The mixture was added dropwise with water (150 ml) and concentrated hydrochloric acid (25 ml) under ice cooling and then stirring was continued at 60° C. for 2 hours. The reaction mixture was separated by adding ethyl acetate (100 ml) and water (150 ml), and the aqueous layer was made alkaline with sodium hydroxide and then extracted with toluene. The organic layer was washed with water and dried over anhydrous sodium sulfate, and then the solvent was evaporated to give N-pentyl-2-(5-imidazolyl-2,3-methylenedioxyphenyl)ethylamine (1.52 g) as an oil.

Workup

  1. temperatureunder reflux
  2. temperatureunder reflux
  3. stirringstirring
  4. waitwas continued at 60° C. for 2 hours
  5. customThe reaction mixture was separated
  6. additionby adding ethyl acetate (100 ml) and water (150 ml)
  7. extractionextracted with toluene
  8. washThe organic layer was washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-643006db8eb1460fa9c4663c4e9f10e3
Source dataset
uspto-grants-1998_09
Patent number
US05807860

Reaction notes

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