Dimethylamine → HCID 13747245, compound

HRID 5221Notes

Reaction equation

HRID 5221 reaction equation
[CH3:1][NH:2][CH3:3].Br[CH2:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:12]([CH:17]=1)[C:13]([O:15][CH3:16])=[O:14])=[O:7].[BH4-].[Na+]>C(O)C.C1COCC1>[CH3:1][N:2]([CH3:3])[CH2:5][CH:6]([C:8]1[CH:9]=[CH:10][C:11]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:12]([CH:17]=1)[C:13]([O:15][CH3:16])=[O:14])[OH:7]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 4311764Sodium borohydrideHCID 11824614Methyl 5-(2-bromoacetyl)-2-(phenylmethoxy)benzoate

Product 1

HCID 13747245HCID 13747245, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dimethylamine (33% in ethanol, 156 ml) was added to a stirred suspension of methyl 5-(bromoacetyl)-2-(phenylmethoxy)benzoate (105.8 g) in absolute ethanol (1l) and THF (1l). The resulting solution was stirred at RT for 2 h, treated with NaBH4 (25 g) and stirred at RT overnight. The solvent was removed in vacuo and H2O (500 ml) was added to the residue. The mixture was extracted with EA (2×500 ml), the combined extracts were washed with H2O and BR, dried (Na2SO4) and concentrated in vacuo. The product was purified twice by [FCS] eluted with EA-methanol-triethylamine (80:20:1) to give the title compound as a fawn solid (59.8 g) m.p. 79-81°.

Workup

  1. stirringstirred at RT overnight
  2. customThe solvent was removed in vacuo and H2O (500 ml)
  3. additionwas added to the residue
  4. extractionThe mixture was extracted with EA (2×500 ml)
  5. washthe combined extracts were washed with H2O and BR
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe product was purified twice by [FCS]
  9. washeluted with EA-methanol-triethylamine (80:20:1)

Sources & evidence

ORD record
ord-cea66657c1d54213bd0be73281450b4e
Source dataset
uspto-grants-1993_09
Patent number
US05243076

Reaction notes

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