1-Isopropylpiperazine → 1-(4-Isopropylpiperazin-1-yl)hex-5-yn-1-one

HRID 1052502ノート

反応式

HRID 1052502 の反応式
[CH:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)([CH3:3])[CH3:2].[C:10](O)(=[O:16])[CH2:11][CH2:12][CH2:13][C:14]#[CH:15].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10](=[O:16])[CH2:11][CH2:12][CH2:13][C:14]#[CH:15])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 780131-IsopropylpiperazineHCID 1430365-Hexynoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 665455341-(4-Isopropylpiperazin-1-yl)hex-5-yn-1-one収率 38.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

1-Isopropylpiperazine (228 mg, 1.78 mmol) was added over a mixture of hex-5-ynoic acid (200 mg, 1.78 mmol), N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (393 mg, 2.05 mmol) and N,N-dimethylpyridin-4-amine (10 mg, 0.05 mmol) in dichloromethane (10 ml) at 0° C. and the resulting mixture was stirred at room temperature overnight. 100 ml of dichloromethane were added and washed with sodium bicarbonate 4%. Then a solution of hydrogen chloride 0.5 N was added to the organic phase. The aquose phase was separated and neutralised with a solution of NaOH 2N and treated with ethyl acetate. The ethyl acetate phase was washed with water and brine, dried over magnesium sulphate and the solvent removed to give 152 mg (34% yield) of the title compound. Purity 90%.

後処理

  1. washwashed with sodium bicarbonate 4%
  2. additionThen a solution of hydrogen chloride 0.5 N was added to the organic phase
  3. customThe aquose phase was separated
  4. additiontreated with ethyl acetate
  5. washThe ethyl acetate phase was washed with water and brine
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent removed

出典と根拠

ORDレコード
ord-cb57b4774c8c4f5cb6b05ce7e4dbace0
出典データセット
uspto-grants-2016_07
特許番号
US09388189B2

反応ノート

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