Dibenzylamine → alpha-[[Bis(phenylmethyl)amino]methyl]-3-(methoxymethyl)-4-(phenylmethoxy)benzenemethanol

HRID 1165276노트

반응식

HRID 1165276 반응식
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:7]([CH2:19][O:20][CH3:21])[CH:6]=1)=[O:4].[CH2:22]([NH:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[C:23]1([CH2:22][N:29]([CH2:2][CH:3]([C:5]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:7]([CH2:19][O:20][CH3:21])[CH:6]=2)[OH:4])[CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

참가 물질

4

반응물 2

HCID 7656DibenzylamineHCID 124989662-Bromo-1-[3-(methoxymethyl)-4-(phenylmethoxy)phenyl]ethanone

생성물 1

HCID 19862717alpha-[[Bis(phenylmethyl)amino]methyl]-3-(methoxymethyl)-4-(phenylmethoxy)benzenemethanol수율 85.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2-bromo-1-[3-(methoxymethyl)-4-(phenylmethoxy)phenyl]ethanone (2.0 g), dibenzylamine (1.2 g) and DEA (0.8 g) in THF (30 ml) was allowed to stand at room temperature for 18 h, filtered and evaporated. The residual oil was dissolved in ethanol (20 ml) and treated portionwise with sodium borohydride (0.23 g), under nitrogen. The mixture was stirred at room temperature for 1 h, treated with methanol (20 ml), and evaporated. The residue was purified by FCC eluting with CX-ER (3:1) to give the title compound as an off-white solid (2.3 g), m.p. 52°-57°, t.l.c. (CX-ER 1:1) Rf 0.5

후처리

  1. filtrationfiltered
  2. customevaporated
  3. dissolutionThe residual oil was dissolved in ethanol (20 ml)
  4. additiontreated portionwise with sodium borohydride (0.23 g), under nitrogen
  5. additiontreated with methanol (20 ml)
  6. customevaporated
  7. customThe residue was purified by FCC
  8. washeluting with CX-ER (3:1)

출처 및 근거

ORD 기록
ord-d6936fe54de6497bac92ee75bf19e192
출처 데이터셋
uspto-grants-1990_03
특허 번호
US04908386

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