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

HRID 279351ノート

反応式

HRID 279351 の反応式
[NH2:1][CH:2]1[CH2:8][CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Cl)=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[NH2:1][CH:2]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:14][C:13]2[CH:16]=[CH:17][C:10]([Cl:9])=[CH:11][CH:12]=2)[CH2:3]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

A solution of 3-aminohomopiperidine (1.71 g, 15 mmol) in CH3CN (45 mL) was treated with p-chlorobenzyl chloride (463 mg, 2.9 mmol) and K2CO3 (828 g, 6 mmol) and heated to 70° C. for 9 h. The reaction mixture was cooled to 25° C. and concentrated to afford a yellow solid. The residue was partitioned between H2O (5 mL) and EtOAc (50 mL), and extracted with EtOAc (2×50 mL). The combined organic extracts were washed with brine (20 mL), dried (Na2SO4) and concentrated. The resulting yellow oil was purified by chromatography (SiO2, 5-20% CH3OH—CH2Cl2 gradient elution) to afford the desired product as a yellow oil (639 mg, 93%).

後処理

  1. temperatureThe reaction mixture was cooled to 25° C.
  2. concentrationconcentrated
  3. customto afford a yellow solid
  4. customThe residue was partitioned between H2O (5 mL) and EtOAc (50 mL)
  5. extractionextracted with EtOAc (2×50 mL)
  6. washThe combined organic extracts were washed with brine (20 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe resulting yellow oil was purified by chromatography (SiO2, 5-20% CH3OH—CH2Cl2 gradient elution)

出典と根拠

ORDレコード
ord-008f99bd4ef24cc2a51d056e6de3a40f
出典データセット
uspto-grants-2002_03
特許番号
US06362177B1

反応ノート

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