Potassium Iodide → HCID 19915644, compound

HRID 1089668Notes

Reaction equation

HRID 1089668 reaction equation
[O:1]1[C:5]2[C:6]([CH:10]3[C:16]4[CH:17]=[C:18]([OH:22])[C:19]([Cl:21])=[CH:20][C:15]=4[CH2:14][CH2:13][N:12]([CH3:23])[CH2:11]3)=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[I-].[K+].[CH3:26][O:27][CH2:28]Cl>C(O)C>[O:1]1[C:5]2[C:6]([CH:10]3[C:16]4[CH:17]=[C:18]([O:22][CH2:26][O:27][CH3:28])[C:19]([Cl:21])=[CH:20][C:15]=4[CH2:14][CH2:13][N:12]([CH3:23])[CH2:11]3)=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 7864Chloromethyl Methyl EtherHCID 9996569HCID 9996569, compound

Product 1

HCID 19915644HCID 19915644, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(+)-5-(7-benzofuranyl)-8-chloro-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ol (1.64 g, 0.005 mol) is suspended in dry ethanol (50 ml). Potassium-tert.-butylate (1.12 g, 0.010 mol) and potassiumiodide (0.10 g) are added. To the resulting solution chloromethyl methyl ether (0.84 g, 0.010 mol) is added. The reaction mixture is stirred for 3 hours. The resulting suspension is filtered and the filtrate evaporated to dryness under reduced pressure. The residue is chromatographed on a silicia-gel column, using dichloromethane/methanol (25:1) as the eluent. The fractions containing the product are collected and evaporated to dryness under reduced pressure.

Workup

  1. filtrationThe resulting suspension is filtered
  2. customthe filtrate evaporated to dryness under reduced pressure
  3. customThe residue is chromatographed on a silicia-gel column
  4. additionThe fractions containing the product
  5. customare collected
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8da0a2b9488a438d90c5349176d7740f
Source dataset
uspto-grants-1992_01
Patent number
US05079243

Reaction notes

Loading…