1-Chloro-4-(chloromethyl)benzene → 3-Amino-1-(4-chlorobenzyl)homopiperidine

HRID 133628ノート

反応式

HRID 133628 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[NH2:16][CH:17]1[CH2:23][CH2:22][CH2:21][CH2:20][NH:19][CH2:18]1>C(#N)C>[NH2:16][CH:17]1[CH2:23][CH2:22][CH2:21][CH2:20][N:19]([CH2:6][C:5]2[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:18]1

参加物

5

反応物 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 2756445Azepan-3-amine

生成物 1

HCID 184262393-Amino-1-(4-chlorobenzyl)homopiperidine収率 93%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

p-Chlorobenzyl chloride (463 mg, 2.9 mmol) and K2CO3 (828 g, 6 mmol) were added to an acetonitrile (45 mL) solution of 3-aminohomopiperidine (1.71 g, 15 mmol), and the resulting mixture was stirred at 70° C. with heating for 9 hours, cooled to 25° C. and concentrated to afford a yellow solid. The resulting residue was partitioned between H2O (5 mL) and ethyl acetate (50 mL) and the aqueous layer was extracted with ethyl acetate (50 mL×2). The organic layers were combined, washed with brine (20 mL), dried (over MgSO4) and concentrated. The obtained yellow oil was purified by column chromatography (SiO2, 5-20% methanol/dichloromethane gradient elution) to afford the objective compounds as yellow oil (639 mg, 93%).

後処理

  1. temperaturewith heating for 9 hours
  2. temperaturecooled to 25° C.
  3. concentrationconcentrated
  4. customto afford a yellow solid
  5. customThe resulting residue was partitioned between H2O (5 mL) and ethyl acetate (50 mL)
  6. extractionthe aqueous layer was extracted with ethyl acetate (50 mL×2)
  7. washwashed with brine (20 mL)
  8. dry with materialdried (over MgSO4)
  9. concentrationconcentrated
  10. customThe obtained yellow oil was purified by column chromatography (SiO2, 5-20% methanol/dichloromethane gradient elution)

出典と根拠

ORDレコード
ord-604b89e912b449709603e513eb5f83ed
出典データセット
uspto-grants-2008_06
特許番号
US07390830B1

反応ノート

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