Dimethylformamide → HCID 60376, compound

HRID 2285725Notes

Reaction equation

HRID 2285725 reaction equation
Cl.[NH:2]1[CH2:7][CH:6]=[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1.CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+].Cl[CH2:32][CH:33]1[CH2:35][CH2:34]1>O>[CH:33]1([CH2:32][N:2]2[CH2:3][CH:4]=[C:5]([C:8]3[C:16]4[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=4)[NH:10][CH:9]=3)[CH2:6][CH2:7]2)[CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 80013(Chloromethyl)cyclopropaneHCID 130190085-Nitro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole--hydrogen chloride (1/1)

Product 1

HCID 60376HCID 60376, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 11.88 g of 3-(1,2,3,6-tetrahydro-4-pyridinyl)-5-nitro-1H-indole hydrochloride, 148 ml of dimethylformamide, 12.72 g of sodium carbonate and 4.8 ml of chloromethylcyclopropane was stirred at 70° C. under an inert atmosphere for 23 hours and the mixture was cooled. 450 ml of distilled water were added to the mixture which was then stirred for one hour and was vacuum filtered. The recovered product was rinsed with water and dried to obtain 10.8 g of raw product. The latter was chromatographed over silica gel and was eluted with a 6-3-1 chloroform-acetone-triethylamine mixture to obtain 8.3 g of 3-(1-cyclopropylmethyl-1,2,3,6-tetrahydro-4-pyridinyl)-5-nitro-1H-indole melting at 187°-188° C.

Workup

  1. temperaturethe mixture was cooled
  2. stirringwas then stirred for one hour
  3. filtrationfiltered
  4. washThe recovered product was rinsed with water
  5. customdried
  6. customto obtain 10.8 g of raw product
  7. customThe latter was chromatographed over silica gel
  8. washwas eluted with a 6-3-1 chloroform-acetone-triethylamine mixture

Sources & evidence

ORD record
ord-69ab4204c38c4dd0babe9d6f151a630b
Source dataset
uspto-grants-1982_04
Patent number
US04324790

Reaction notes

Loading…