Chloromethyl Methyl Ether → HCID 19915640, compound

HRID 1089670Notes

Reaction equation

HRID 1089670 reaction equation
[O:1]1[C:5]2[C:6]([CH:10]3[C:16]4[CH:17]=[C:18]([OH:24])[C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:15]=4[CH2:14][CH2:13][N:12]([CH3:25])[CH2:11]3)=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.[CH3:26][O:27][CH2:28]Cl>O1CCCC1>[O:1]1[C:5]2[C:6]([CH:10]3[C:16]4[CH:17]=[C:18]([O:24][CH2:26][O:27][CH3:28])[C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:15]=4[CH2:14][CH2:13][N:12]([CH3:25])[CH2:11]3)=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7864Chloromethyl Methyl EtherHCID 9840885HCID 9840885, compound

Product 1

HCID 19915640HCID 19915640, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(+)-5-(2,3-dihydrobenzofuran-7-yl)-3-methyl-8-nitro-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ol (68.0 mg, 2.0 mmol) and potassium-tert-butylate (24.0 mg, 2.2 mmol) are dissolved in dry tetrahydrofuran (10 ml) at 23° C. Chloromethyl methyl ether (20.0 mg, 2.5 mmol) is added. The reaction mixture is stirred for 22 hours, filtered and the filtrate evaporated to dryness under reduced pressure. The resulting light yellow oil is purified using reverse phase HPLC (column 16 mm×250 mm, C18 7μ; eluent aceticnitril/0.1M ammoniumsulphate pH 3.3 (30:70), isocratic). The fractions containing the product are pooled. The pH is adjusted to 9.0, and the product extracted into dichloromethane. The organic phase is evaporated to dryness under reduced pressure.

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated to dryness under reduced pressure
  3. customThe resulting light yellow oil is purified
  4. additionThe fractions containing the product
  5. extractionthe product extracted into dichloromethane
  6. customThe organic phase is evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-17337a63afca4244980b0a983aec0b8f
Source dataset
uspto-grants-1992_01
Patent number
US05079243

Reaction notes

Loading…