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

HRID 387619ノート

反応式

HRID 387619 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-450d2f7c2104419495a4bd4d5329b7bd
出典データセット
uspto-grants-2013_02
特許番号
US08372864B2

反応ノート

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