Potassium Iodide → HCID 18982209, compound

HRID 1440819Notes

Reaction equation

HRID 1440819 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[C:14]2[O:13][CH2:12][CH2:11][O:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.Br.[F:16][C:17]1[CH:31]=[CH:30][C:20]([C:21]([CH:23]2[CH2:29][CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[O:22])=[CH:19][CH:18]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(C(CC)=O)C.CC(C)=O.CCOCC.CO>[ClH:1].[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([CH:23]2[CH2:29][CH2:28][CH2:27][N:26]([CH2:2][CH2:3][O:4][C:5]3[C:14]4[O:13][CH2:12][CH2:11][O:10][C:9]=4[CH:8]=[CH:7][CH:6]=3)[CH2:25][CH2:24]2)=[O:22])=[CH:30][CH:31]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 114699561,4-Benzodioxin, 5-(2-chloroethoxy)-2,3-dihydro-HCID 18982196HCID 18982196, compound

Product 1

HCID 18982209HCID 18982209, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 7288Ethyl ketoneSolventHCID 21584533Acetone diethyletherSolvent

Procedure

A mixture of 5 g of 5-(2-chloroethoxy)-1,4-benzodioxane, 7.8 g of 4-(4-fluorobenzoyl)perhydroazepine hydrobromide (described in Patent EP 389,352), 1 g of potassium iodide and 6.5 g of potassium carbonate in 100 ml of diethyl ketone is maintained at 100 C. for 24 hours. The inorganic salts are then filtered off and the filtrate is concentrated under vacuum. The residue is purified by chromatography on a column of silica, with a dichloromethane/methanol/aqueous ammonia (97/3/0.3) eluent mixture. The base obtained is salified with hydrochloric methanol in an acetone/ether mixture. Melting point: 106°-107° C.

Workup

  1. temperatureis maintained at 100 C
  2. filtrationThe inorganic salts are then filtered off
  3. concentrationthe filtrate is concentrated under vacuum
  4. customThe residue is purified by chromatography on a column of silica, with a dichloromethane/methanol/aqueous ammonia (97/3/0.3) eluent mixture
  5. customThe base obtained

Sources & evidence

ORD record
ord-0d2c21b63c4a43dab9d4913c9d180fc0
Source dataset
uspto-grants-1996_03
Patent number
US05500443

Reaction notes

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