Hydrochloric Acid → HCID 9951606, compound

HRID 985599Notes

Reaction equation

HRID 985599 reaction equation
Cl.[CH3:2][C:3]1([CH2:19][N:20]2[CH2:25][CH2:24][CH:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:22][CH2:21]2)[O:18][C:6]2=[C:7]([CH3:17])[C:8]3[CH2:9][CH2:10][N:11](C=O)[C:12]=3[C:13]([CH3:14])=[C:5]2[CH2:4]1.Cl.[OH-].[Na+]>CO>[CH3:2][C:3]1([CH2:19][N:20]2[CH2:25][CH2:24][CH:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:22][CH2:21]2)[O:18][C:6]2=[C:7]([CH3:17])[C:8]3[CH2:9][CH2:10][NH:11][C:12]=3[C:13]([CH3:14])=[C:5]2[CH2:4]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22506870HCID 22506870, compound

Product 1

HCID 9951606HCID 9951606, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

3,5,6,7-Tetrahydro-2,4,8-trimethyl-2-[(4-phenylpiperidino)methyl]-2H-furo[2,3-f]indole-5-carbaldehyde hydrochloride (309 mg, 0.7 mmol) was dissolved in methanol (5 ml). To the solution was added concentrated hydrochloric acid (1 ml) and stirred for 1 hour at 60° C. under argon atmosphere. The reaction mixture was cooled to room temperature, made weakly basic with 12N sodium hydroxide, and extracted with ethyl acetate. The extract was washed with saturated brine and dried over sodium sulfate, and the solvent was removed under reduced pressure. The resultant oil was crystallized from hexane to obtain 203 mg of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe resultant oil was crystallized from hexane

Sources & evidence

ORD record
ord-7b5610816c45447f9460e2f63a9f5f7b
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Reaction notes

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