Methyl iodide → HCID 21555000, compound

HRID 267551Notes

Reaction equation

HRID 267551 reaction equation
[CH2:1]1[CH:16]2[N:4]([CH2:5][CH2:6][C:7]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[NH:9][C:8]=32)[CH2:3][CH2:2]1.[H-].[Na+].[CH3:19]I>CN(C)C=O>[CH3:19][N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]2[CH2:6][CH2:5][N:4]3[CH:16]([C:8]1=2)[CH2:1][CH2:2][CH2:3]3

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 372331NSC647389

Product 1

HCID 21555000HCID 21555000, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

2,3,5,6,11,11b-Hexahydro-1H-indolizino[8,7-b]-indole (8.49 g.) is stirred for 1 hour at 25°C. in dimethylformamide (200 ml.) containing sodium hydride (2.11 g. of a 50% mineral oil dispersion). Methyl iodide (6.25 g.) in dimethylformamide (25 ml.) is added and the mixture is stirred at 25°C. for 16 hours. The dimethylformamide is distilled off, and the residue is dissolved in chloroform and washed with aqueous potassium bicarbonate and water, and dried. The product is chromatographed on neutral alumina to give 2,3,5,6,11,11b-hexahydro-11-methyl-1H-indolizino[8,7-b]indole as a clear oil (5.88 g.).

Workup

  1. distillationThe dimethylformamide is distilled off
  2. dissolutionthe residue is dissolved in chloroform
  3. washwashed with aqueous potassium bicarbonate and water
  4. customdried
  5. customThe product is chromatographed on neutral alumina

Sources & evidence

ORD record
ord-e59f2ff5d65e46b3bcd979769ed95266
Source dataset
uspto-grants-1976_03
Patent number
US03943148

Reaction notes

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