Triethylamine → 4-Methyloxycarbonylmethylaminophenyl [1-(4-pyridyl)piperidin-4-yl]acetate

HRID 1291880ノート

反応式

HRID 1291880 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH2:14]([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[CH3:15]>ClCCl>[N:8]1[CH:5]=[CH:4][C:14]([N:16]2[CH2:19][CH2:20][CH:6]([CH2:7][C:2]([O:1][C:2]3[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=3)=[O:1])[CH2:18][CH2:17]2)=[CH:15][CH:9]=1

参加物

4

反応物 2

HCID 8471TriethylamineHCID 422581Methyl 2-((4-hydroxyphenyl)amino)acetate

生成物 1

HCID 196893984-Methyloxycarbonylmethylaminophenyl [1-(4-pyridyl)piperidin-4-yl]acetate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

A solution of the foam in dry dichloromethane (5 ml) was added dropwise to a stirred solution of methyl N-(4-hydroxyphenyl)glycinate (210 mg) and triethylamine (0.33 ml) in dry dichloromethane (10 ml) and the mixture stirred for 16 hours. The mixture was diluted with dichloromethane, washed with water, dried and evaporated. Purification by flash chromatography on silica, eluting with 0-10% v/v methanol/dichloromethane and trituration of the resulting gum with diethyl ether gave the title compound, 80 mg, as a white solid: m.p. 120°-122° C.; NMR(d6DMSO), δ 8.13(2H,d), 6.84(2H,d), 6.81(2H,d), 6.54(2H,d), 6.01(1H,t), 3.96(2H,bd), 3.90(2H,d), 3.66(3H,s), 2.90(2H,dt), 2.50(2H,d +DMSO), 2.07(1H,m), 1.81(2H,bd), 1.30(2H,dq); m/e 384(M+H)+ ; calculated for C21 H25N3O4. 0.5 H2O: C, 64.3; H, 6.6; N, 10.7. found: C, 64.2; H, 6.3; N, 10.7%.

後処理

  1. washwashed with water
  2. customdried
  3. customevaporated
  4. customPurification by flash chromatography on silica
  5. washeluting with 0-10% v/v methanol/dichloromethane and trituration of the resulting gum with diethyl ether

出典と根拠

ORDレコード
ord-a5d2c43c4b0c4bddb525bc809af658b9
出典データセット
uspto-grants-1998_05
特許番号
US05753659

反応ノート

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