Triethylamine → 1-(3-Coumarinylcarbonyl)-4-(3,4,5-trimethoxybenzyl)piperazine

HRID 2108101노트

반응식

HRID 2108101 반응식
[O:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]([OH:14])=O)[C:2]1=[O:3].Cl.Cl.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:29]=[C:30]([O:34][CH3:35])[C:31]=1[O:32][CH3:33])[CH2:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>CCCCCC.C(OCC)(=O)C.O.CN(C)C=O>[O:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]([N:26]2[CH2:25][CH2:24][N:23]([CH2:22][C:21]3[CH:29]=[C:30]([O:34][CH3:35])[C:31]([O:32][CH3:33])=[C:19]([O:18][CH3:17])[CH:20]=3)[CH2:28][CH2:27]2)=[O:14])[C:2]1=[O:3]

참가 물질

9

반응물 4

HCID 8471TriethylamineHCID 10752Coumarin-3-Carboxylic AcidHCID 76257Diethyl cyanophosphonateHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochloride

생성물 1

HCID 148497021-(3-Coumarinylcarbonyl)-4-(3,4,5-trimethoxybenzyl)piperazine수율 16.9%

시약·촉매·용매 4

HCID 962Water용매2회HCID 6228Dimethylformamide용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of coumarin-3-carboxylic acid (0.9 g), 1(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (1.7 g), triethylamine (1.8 g) and N,N-dimethylformamide (20 ml) is added dropwise at room temperature diethyl cyanophosphonate (1.8 ml), followed by stirring for one hour. After addition of water (50 ml), the reaction mixture is left standing for 30 minutes, followed by addition of water (150 ml), ethyl acetate (200 ml) and hexane (50 ml). The mixture is vigorously mixed and the organic layer is separated. The organic layer is washed with water, dried, and concentrated under reduced pressure. The residue is purified by means of a silica gel column chromatography(hexane:acetone=1:1-1:2) to give an oily product, which is crystallized from a mixture of acetone and ethyl ether to afford 1-(3-coumarinylcarbonyl)-4-(3,4,5-trimethoxybenzyl)piperazine (0.35 g) as colorless needles, m.p. 171°-173° C.

후처리

  1. waitthe reaction mixture is left
  2. waitstanding for 30 minutes
  3. additionThe mixture is vigorously mixed
  4. customthe organic layer is separated
  5. washThe organic layer is washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by means of a silica gel column chromatography(hexane:acetone=1:1-1:2)
  9. customto give an oily product, which
  10. customis crystallized from a mixture of acetone and ethyl ether

출처 및 근거

ORD 기록
ord-2fb59b6ff0f84f86af51d2af3a2b22a0
출처 데이터셋
uspto-grants-1990_06
특허 번호
US04937246

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