Potassium Bicarbonate → HCID 9950608, compound

HRID 1591046Notes

Reaction equation

HRID 1591046 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][CH2:10]Cl)=[CH:3][CH:2]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[S:26][CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:16][CH:15]=1.C(=O)(O)[O-].[K+]>C(#N)C>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]2[S:26][CH2:25][CH2:24][N:23]([CH2:10][CH2:9][CH2:8][CH2:7][C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[CH2:22][CH2:21]2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 516893Potassium BicarbonateHCID 109539414-(4-Chlorobutyl)pyridineHCID 19766136HCID 19766136, compound

Product 1

HCID 9950608HCID 9950608, compoundYield 37.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 25 mL of acetonitrile is added 1-(4-pyridinyl)-4-chlorobutane (2.00 g, 11.8 mmol), hexahydro-7-(4 methoxyphenyl)-1,4-thiazepine (Example 1) (2.63 g, 11.8 mmol), and anhydrous potassium bicarbonate (2.65 g, 47.2 mmol). The reaction mixture is heated to reflux under an atmosphere of nitrogen for 24 hours. The reaction mixture is then filtered, the filtrate concentrated, and the resulting residue is purified by column chromatography on silica eluting with 98% chloroform, 2% methanol, and 0.1% anhydrous ammonia to yield 1.58 g of the desired product; m/z 356.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux under an atmosphere of nitrogen for 24 hours
  3. filtrationThe reaction mixture is then filtered
  4. concentrationthe filtrate concentrated
  5. customthe resulting residue is purified by column chromatography on silica eluting with 98% chloroform, 2% methanol, and 0.1% anhydrous ammonia

Sources & evidence

ORD record
ord-868e1bbadb124d828005a4539eb3e35e
Source dataset
uspto-grants-1993_04
Patent number
US05206233

Reaction notes

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