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

HRID 1165276Notes

Reaction equation

HRID 1165276 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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

Workup

  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)

Sources & evidence

ORD record
ord-d6936fe54de6497bac92ee75bf19e192
Source dataset
uspto-grants-1990_03
Patent number
US04908386

Reaction notes

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