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

HRID 259081Notes

Reaction equation

HRID 259081 reaction equation
Cl(O)(=O)(=O)=O.[CH2:6]([C:8]1[CH2:9][CH2:10][CH2:11][N:12]2[C:17]=1[C:16]1[NH:18][C:19]3[C:24]([C:15]=1[CH2:14][CH2:13]2)=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:7].[OH-:25].[Na+].[CH2:27]=O>ClCCl.O>[OH:25][CH2:27][C:8]1([CH2:6][CH3:7])[CH:17]2[N:12]([CH2:13][CH2:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:18][C:16]=32)[CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 86734944HCID 86734944, compound

Product 1

HCID 658931-Hydroxymethyl-1-ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

10.0 g. (28.5 moles) of 1-ethyl-2,3,4,6,7,12-hexahydro-indolo[2,3-a]quinolizine perchlorate are dissolved in 100 ml. of dichloromethane, and 75 ml. of distilled water and 20 ml. of a 2N sodium hydroxide solution are added to the dichloromethane solution in argon atmosphere under constant stirring. The reaction mixture is stirred for 10 minutes, thereafter the organic phase is separated, dried over anhydrous potassium carbonate, and filtered. The filtrate is concentrated in vacuo, under argon atmosphere, to a final volume of 15 ml., and 2.0 g. (66.8 mmoles) of paraformaldehyde are added to the concentrate. The solvent is evaporated in vacuo, and the residue is heated at 160°-170 ° C. (bath temperature) for 4 hours in a closed vessel.

Workup

  1. customthe organic phase is separated
  2. dry with materialdried over anhydrous potassium carbonate
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated in vacuo, under argon atmosphere
  5. customThe solvent is evaporated in vacuo
  6. temperaturethe residue is heated at 160°-170 ° C. (bath temperature) for 4 hours in a closed vessel

Sources & evidence

ORD record
ord-a98a69236b374c4bb58532c7a6ada6d3
Source dataset
uspto-grants-1977_07
Patent number
US04036841

Reaction notes

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