Pyridine → HCID 14954045, compound

HRID 863666Notes

Reaction equation

HRID 863666 reaction equation
[C:1]([O:4][C:5](=O)C)(=[O:3])[CH3:2].[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]3N=CC=C[C:15]3=2)[CH:10]=[CH:9]1.N1[CH:26]=[CH:25][CH:24]=[CH:23]C=1>>[C:1]([O:4][CH2:5][CH:25]1[CH2:24][CH2:23][N:8]2[C:16]3[C:11]([CH:10]=[C:9]2[CH2:26]1)=[CH:12][CH:13]=[CH:14][CH:15]=3)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 178420737HCID 178420737, compound

Product 1

HCID 14954045HCID 14954045, compound

Procedure

11.4 g of acetic anhydride were added to a solution of 11.0 g of the pyridoindole from c) in 100 ml of pyridine and the resulting solution was stirred under a nitrogen atmosphere for 18 hours. The majority of the pyridine was removed by evaporation and the residue was acidified with 2M hydrochloric acid. The mixture was extracted with diethyl ether and the combined extracts were washed with sodium bicarbonate solution and with water. The extracts were dried and evaporated to dryness to give 11.25 g of 8-(acetoxymethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indole of melting point 63°-64° C.

Workup

  1. customThe majority of the pyridine was removed by evaporation
  2. extractionThe mixture was extracted with diethyl ether
  3. washthe combined extracts were washed with sodium bicarbonate solution and with water
  4. customThe extracts were dried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-265e4f2d58d443ff8bb53526f0411de6
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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