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

HRID 1052502노트

반응식

HRID 1052502 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-cb57b4774c8c4f5cb6b05ce7e4dbace0
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388189B2

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