1-Hydroxymethyl-1-ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizine → HCID 21423108, compound

HRID 259083Notes

Reaction equation

HRID 259083 reaction equation
[OH:1][CH2:2][C:3]1([CH2:20][CH3:21])[CH:12]2[N:7]([CH2:8][CH2:9][C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[NH:13][C:11]=32)[CH2:6][CH2:5][CH2:4]1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([O:35][CH3:36])[C:32]=1[O:33][CH3:34])[C:27](Cl)=[O:28]>N1C=CC=CC=1>[CH3:36][O:35][C:31]1[CH:30]=[C:26]([CH:25]=[C:24]([O:23][CH3:22])[C:32]=1[O:33][CH3:34])[C:27]([O:1][CH2:2][C:3]1([CH2:20][CH3:21])[CH:12]2[N:7]([CH2:8][CH2:9][C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[NH:13][C:11]=32)[CH2:6][CH2:5][CH2:4]1)=[O:28]

Participants

4

Reactant 2

HCID 658931-Hydroxymethyl-1-ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-

Product 1

HCID 21423108HCID 21423108, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.30 g. (4.58 mmoles) of 1-hydroxymethyl-1-ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizine and 2.30 g. (10 mmoles) of 3,4,5-trimethoxybenzoyl chloride are dissolved in 15 ml. of absolute pyridine, and the solution is heated on a steam bath for 10 hours under a reflux condenser. The solution is evaporated in vacuo, and the oily residue is stirred first with a 5% sodium hydrocarbonate solution and then with distilled water. The separated solids are filtered off, dried, and recrystallized from methanol. 2.05 g. (93.5%) of the title compound are obtained as white crystals melting at 170°-171° C.

Workup

  1. customThe solution is evaporated in vacuo
  2. filtrationThe separated solids are filtered off
  3. customdried
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-9b264384638e4e5c8cbbfa9e36feabf8
Source dataset
uspto-grants-1977_07
Patent number
US04036841

Reaction notes

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