N-Methylphenylethanolamine → HCID 21842621、化合物

HRID 1737450

反応式

HRID 1737450 の反応式
[CH3:1][NH:2][CH2:3][CH:4]([OH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)C(C)C)(C)C>C1COCC1>[OH:11][CH:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][N:2]([CH3:1])[S:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:20])=[O:19]

参加物

5

反応物 3

HCID 913N-MethylphenylethanolamineHCID 7369Benzenesulfonyl chlorideHCID 81531Diisopropylethylamine

生成物 1

HCID 21842621HCID 21842621、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of α-(methylaminomethyl)benzyl alcohol (1.00 g, 6.61 mmol) in 15 mL of THF was cooled in an ice bath. Benzenesulfonyl chloride (0.886 mL, 1.23 g, 6.94 mmol) and N,N-diisopropylethylamine (2.3 mL, 1.7 g, 13 mmol) were added and mixture was allowed to warm to room temperature. After 30 min, the solvent was evaporated and the residue was partitioned between 50 mL of ethyl acetate and 40 mL of saturated aqueous sodium bicarbonate. The aqueous layer was extracted with 2×50 mL of ethyl acetate. The combined organic layers were washed with 50 mL of brine, dried over sodium sulfate, and evaporated. Purification by flash column chromatography on silica gel, eluting with 20-50% ethyl acetate in hexane, gave the title compound in quantitative yield.

後処理

  1. customthe solvent was evaporated
  2. customthe residue was partitioned between 50 mL of ethyl acetate and 40 mL of saturated aqueous sodium bicarbonate
  3. extractionThe aqueous layer was extracted with 2×50 mL of ethyl acetate
  4. washThe combined organic layers were washed with 50 mL of brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customPurification by flash column chromatography on silica gel
  8. washeluting with 20-50% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-ba598985bff041bf90162b74bd66b628
出典データセット
uspto-grants-1999_10
特許番号
US05962462

関連ノート

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