Sodium Hydroxide → N-[2-(2-bromophenyl)ethyl]heptan-4-amine

HRID 387619Notes

Reaction equation

HRID 387619 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][NH2:6].[CH3:11][CH2:12][CH2:13][C:14](=O)[CH2:15][CH2:16][CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl.C(O)(=O)C>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][NH:6][CH:14]([CH2:15][CH2:16][CH3:17])[CH2:13][CH2:12][CH3:11]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 312464-HeptanoneHCID 27340912-BromophenethylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 68471618N-[2-(2-bromophenyl)ethyl]heptan-4-amine

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

10 g of 2-bromophenethylamine and 5.71 g of 4-heptanone are dissolved in 250 cm3 of 1,2-dichloroethane at a temperature close to 20° C. 14.84 g of sodium triacetoxyborohydride and 2.9 cm3 of glacial acetic acid are added to the reaction medium. Stirring is continued for 20 h. 300 cm3 of 1M sodium hydroxide are added to the reaction medium. The aqueous phase is extracted with 3 lots of 100 cm3 of ethyl acetate. The organic phases are combined and washed with 4 lots of 100 cm3 of water then 100 cm3 of a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated using a rotary evaporator under reduced pressure (5 kPa). The yellow liquid obtained is purified by flash chromatography over silica (column: 400 g; particle size: 20-40 μm, spherical; flow rate: 30 cm3/min; eluent: 100% heptane to 70% ethyl acetate/30% heptane gradient). After concentrating the fractions under reduced pressure, 17.33 g of N-[2-(2-bromophenyl)ethyl]heptan-4-amine are obtained.

Workup

  1. customclose to 20° C
  2. extractionThe aqueous phase is extracted with 3 lots of 100 cm3 of ethyl acetate
  3. washwashed with 4 lots of 100 cm3 of water
  4. dry with material100 cm3 of a saturated aqueous solution of sodium chloride, dried over magnesium sulfate
  5. concentrationconcentrated
  6. customa rotary evaporator under reduced pressure (5 kPa)
  7. customThe yellow liquid obtained
  8. customis purified by flash chromatography over silica (column: 400 g; particle size: 20-40 μm, spherical; flow rate: 30 cm3/min; eluent: 100% heptane to 70% ethyl acetate/30% heptane gradient)
  9. concentrationAfter concentrating the fractions under reduced pressure, 17.33 g of N-[2-(2-bromophenyl)ethyl]heptan-4-amine
  10. customare obtained

Sources & evidence

ORD record
ord-450d2f7c2104419495a4bd4d5329b7bd
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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