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

HRID 2108101ノート

反応式

HRID 2108101 の反応式
[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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2fb59b6ff0f84f86af51d2af3a2b22a0
出典データセット
uspto-grants-1990_06
特許番号
US04937246

反応ノート

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