Hydrochloric Acid → HCID 4716710, compound

HRID 2393291Notes

Reaction equation

HRID 2393291 reaction equation
[CH2:1]([NH2:6])[CH2:2][CH2:3][CH2:4][CH3:5].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:16][CH3:17])=[C:12]([CH:15]=1)[CH:13]=O.[BH4-].[Na+].Cl.[OH-].[Na+]>O.C(O)C>[CH2:1]([NH:6][CH2:13][C:12]1[CH:15]=[C:8]([Br:7])[CH:9]=[CH:10][C:11]=1[O:16][CH3:17])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8060PentylamineHCID 14798Sodium HydroxideHCID 906845-Bromo-2-methoxybenzaldehydeHCID 4311764Sodium borohydride2×

Product 1

HCID 4716710HCID 4716710, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl alcohol (150 ml) and n-pentylamine (12.7 g, 0.146 mol) were added to 5-bromo-2-methoxybenzaldehyde (30.0 g, 0.14 mol), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was cooled to 5° C., added with sodium borohydride (7.9 g, 0.209 mol), and then stirred at room temperature for 8 hours. The reaction mixture was added with water (50 ml) and aqueous 6N hydrochloric acid to decompose excess sodium borohydride, made alkaline with 25% aqueous sodium hydroxide, and extracted with toluene. The extract was washed with saturated brine and dried over anhydrous sodium sulfate, and then, the solvent was evaporated to give N-pentyl-(5-bromo-2-methoxyphenyl) methylamine (38.0 g).

Workup

  1. temperatureThe reaction mixture was cooled to 5° C.
  2. stirringstirred at room temperature for 8 hours
  3. extractionextracted with toluene
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0abe130d649f4d2ab21613a3195721be
Source dataset
uspto-grants-1998_09
Patent number
US05807860

Reaction notes

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