1-Isopropylpiperazine → 1-iso-Propyl-4-(pent-4-yn-1-yl)piperazine

HRID 1487254ノート

反応式

HRID 1487254 の反応式
[CH3:1][CH:2]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)[CH3:3].Cl[CH2:11][CH2:12][CH2:13][C:14]#[CH:15].C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH:2]([N:4]1[CH2:9][CH2:8][N:7]([CH2:15][CH2:14][CH2:13][C:12]#[CH:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:1]

参加物

5

反応物 3

HCID 780131-IsopropylpiperazineHCID 843081-Pentyne, 5-chloro-HCID 516892Sodium Bicarbonate

生成物 1

HCID 901770341-iso-Propyl-4-(pent-4-yn-1-yl)piperazine収率 35.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 1-(1-methylethyl)piperazine (6 g, 46.8 mmol), 5-chloro-1-pentyne (4.91 mL, 46.8 mmol) and sodium bicarbonate (3.93 g, 46.8 mmol) in N,N-dimethylformamide (75 mL) was heated at 80° C. overnight. The reaction mixture was cooled to room temperature then partitioned between ether (100 mL) and water (100 mL). The organic phase was washed with brine (25 mL) then dried using a hydrophobic frit and evaporated. The crude material was purified on a 50 g SCX cartridge (preconditioned with MeOH) eluted with MeOH and flushed with 2M NH3/MeOH. The appropriate fractions were concentrated and dried under vacuum to obtain the title compound as a light brown oil (3.22 g).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthen partitioned between ether (100 mL) and water (100 mL)
  3. washThe organic phase was washed with brine (25 mL)
  4. customthen dried
  5. customevaporated
  6. customThe crude material was purified on a 50 g SCX cartridge (preconditioned with MeOH)
  7. washeluted with MeOH
  8. customflushed with 2M NH3/MeOH
  9. concentrationThe appropriate fractions were concentrated
  10. customdried under vacuum

出典と根拠

ORDレコード
ord-bc467dae779d42d7a9f9dcd2e2b5372d
出典データセット
uspto-grants-2016_08
特許番号
US09428512B2

反応ノート

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