Thionyl Chloride → HCID 20400816, compound

HRID 1980874Notes

Reaction equation

HRID 1980874 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH3:21])[C:13]=1[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1.C(=O)(O)[O-].[Na+]>>[Cl:3][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH3:21])[C:13]=1[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 20400806HCID 20400806, compound

Product 1

HCID 20400816HCID 20400816, compound

Procedure

Thionyl chloride (0.36 ml) is combined with 3-(6-hydroxyhexyl)-1methyl-2-(3-pyridyl)indole (1.37 g) at 0°. The mixture is then stirred at room temperature for 1 hour. Saturated aqueous sodium bicarbonate is added and the mixture is extracted with dichloromethane. The extract is washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to yield the crude chloride, 3-(6-chlorohexyl)-1-methyl-2-(3-pyridyl)indole. 3-(6-Chlorohexyl)-1-methyl-2-(3-pyridyl)indole (0.5 g) is combined with dimethyl malonate (792 mg), potassium carbonate (790 mg) and dimethylformamide (11.6 ml) and the mixture is heated at 80°-90° for 18 hours under nitrogen. The mixture is poured into ice water (80 ml), and acidified with 1N NCl and washed with ether. The aqueous layer is adjusted to pH 6 and extracted with ether which is then dried over anhydrous magnesium sulfate and concentrated to yield 3-[7,7-(bis-methoxycarbonyl)heptyl]-1-methyl-2 -(3-pyridyl)indole.

Workup

  1. extractionthe mixture is extracted with dichloromethane
  2. washThe extract is washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad72dc8dff9d421e8664772029f945dc
Source dataset
uspto-grants-1985_04
Patent number
US04511573

Reaction notes

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