Phenyl glycidyl ether → HCID 22154115、化合物

HRID 622741ノート

反応式

HRID 622741 の反応式
[ClH:1].[NH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[O:13]1[CH:15]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14]1>C(N(CC)CC)C>[ClH:1].[OH:13][CH:15]([CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:14][NH:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1

参加物

4

反応物 2

HCID 31217Phenyl glycidyl etherHCID 221541064-(2-Aminoethoxy)phenol--hydrogen chloride (1/1)

生成物 1

HCID 22154115HCID 22154115、化合物収率 15.6%

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

A mixture of p-(2-aminoethoxy)phenol hydrochloride, (1.89 g) triethylamine (1.01 g) and 1,2-epoxy-3-phenoxy-propane (1.5 g) was heated under reflux for 24 hours. The reaction mixture was cooled and the solvent was evaporated. The residue was partitioned between dichloromethane (100 ml) and 10% w/v potassium carbonate solution. The organic layer was separated, dried (MgSO4), and the solvent was evaporated. The residual oil was dissolved in ethyl acetate and dry hydrogen chloride was passed through the solution until no further solid precipitated. The precipitate was collected and recrystallised from methanol and ethyl acetate to give p-(2-[2-hydroxy-3-phenoxypropylamino]ethoxy)phenol hydrochloride (0.53 g) mp, 171° C.; microanalysis: found C, 60.3; H, 6.7; N, 4.0; Cl, 10.6%; required for C17H22NClO4 : C, 60.1; H, 6.5; N, 4.1; Cl, 10.5% NMR: 3.09 (dd, 1H, CHOH.CH2NH), 3.28 (dd, 1H, CHOH.CH2NH), 3.47 (t, 2H, NHCH2CH2), 4.15 (m, 2H, NHCH2CH2), 4.25 (m, 1H, CHOH), 5.01 (br s, 1H, CHOH), 6.67+6.79 (2d, 4 aromatic H), 6.92 (m, 3 aromatic H), 7.26 (t, 2 aromatic H), 9.1 (br s, NH2+ +phenolic OH). [Note: p-(2-[(2-hydroxy-3-phenoxypropylamino]ethoxy)phenol in addition to being a valuable intermediate also shows significant thermogenic properties in its own right (sub-cut.ED50 in test (b): 0.51 mg/kg; SI in test (c) >100) and is provided together with its pharmaceutically acceptable salts, and compositions, as a further feature of the invention.]

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent was evaporated
  5. customThe residue was partitioned between dichloromethane (100 ml) and 10%
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. customthe solvent was evaporated
  9. dissolutionThe residual oil was dissolved in ethyl acetate
  10. customprecipitated
  11. customThe precipitate was collected
  12. customrecrystallised from methanol and ethyl acetate

出典と根拠

ORDレコード
ord-efe3667ab08345d3b428dca8dceca8ae
出典データセット
uspto-grants-1988_09
特許番号
US04772631

反応ノート

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