Formaldehyde → (+/-)-1-Ethyl-1-(hydroxymethyl)-1,2,3,4,6,7-hexahydro-indolo[2,3-a]quinolizine

HRID 1707331Notes

Reaction equation

HRID 1707331 reaction equation
[CH2:1]([C:3]1[CH2:4][CH2:5][CH2:6][N:7]2[C:12]=1[C:11]1[NH:13][C:14]3[C:19]([C:10]=1[CH2:9][CH2:8]2)=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH3:2].[CH2:20]=[O:21].O>CC(C)=O>[CH2:1]([C:3]1([CH2:20][OH:21])[C:12]2[N:7]([CH2:8][CH2:9][C:10]3[C:11]=2[N:13]=[C:14]2[C:19]=3[CH:18]=[CH:17][CH:16]=[CH:15]2)[CH2:6][CH2:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 962WaterHCID 11139628HCID 11139628, compound

Product 1

HCID 18963247(+/-)-1-Ethyl-1-(hydroxymethyl)-1,2,3,4,6,7-hexahydro-indolo[2,3-a]quinolizine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

37.8 g (0.15 moles) of 1-ethyl-2,3,4,6,7,12-hexahydro-indolo[2,3-a]quinolizine are dissolved in 100 ml of acetone, 5 g of paraformaldehyde are added thereto and the mixture is stirred at room temperature for an hour and a half. Then 30 ml of distilled water are added to the mixture within 15 minutes and the stirring is continued for another hour at O° C. The precipitated title compound obtained in the form of orange-colored crystals is filtered off and washed in two portions under altogether 20 ml of acetone, at 0° C. Weight: 34.13 g (80.7%), melting point: 111°-113° C.

Workup

  1. waitthe stirring is continued for another hour at O° C
  2. customThe precipitated title compound
  3. customobtained in the form of orange-colored crystals
  4. filtrationis filtered off
  5. washwashed in two portions under altogether 20 ml of acetone, at 0° C

Sources & evidence

ORD record
ord-f5ec78b8c0344a8496f24edcc5d5ed55
Source dataset
uspto-grants-1994_10
Patent number
US05352790

Reaction notes

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