Potassium Carbonate → HCID 22154184, compound

HRID 1110770Notes

Reaction equation

HRID 1110770 reaction equation
[CH2:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH2:3][NH:2]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.CC1C=CC(S(O[CH2:25][CH:26]2[CH2:31][CH2:30][N:29]([C:32](=[O:40])[C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=3)[CH2:28][CH2:27]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:39][C:35]1[CH:34]=[C:33]([CH:38]=[CH:37][CH:36]=1)[C:32]([N:29]1[CH2:28][CH2:27][CH:26]([CH2:25][N:2]2[CH2:3][CH2:4][C:5]3[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[NH:7][C:6]=3[CH2:1]2)[CH2:31][CH2:30]1)=[O:40]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 107838Tetrahydro-beta-carbolineHCID 14577395HCID 14577395, compound

Product 1

HCID 22154184HCID 22154184, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1.7 g (10 mmol) of 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole, 3,9 g (10 mmol) of [1-(3-methylbenzoyl)-4-piperidyl]methyl 4-methylbenzenesulphonate, 2.9 g (20 mmol) of potassium carbonate and 25 ml of dimethylformamide are introduced under an argon atmosphere into a 100-ml round-bottomed flask. The mixture is stirred at 100° C. for 5 h and hydrolysed, and the aqueous phase extracted with ethyl acetate. The organic phase is washed with water and then with saturated aqueous sodium chloride solution and dried over sodium sulphate, and the solvents are evaporated off under reduced pressure. The residue is purified by chromatography on a silica column, eluting with a 9:1 dichloromethane/methanol mixture, and, after recrystallization in ethyl acetate, 1.2 g of pure base are obtained.

Workup

  1. extractionhydrolysed, and the aqueous phase extracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialwith saturated aqueous sodium chloride solution and dried over sodium sulphate
  4. customthe solvents are evaporated off under reduced pressure
  5. customThe residue is purified by chromatography on a silica column
  6. washeluting with a 9:1 dichloromethane/methanol mixture
  7. customafter recrystallization in ethyl acetate

Sources & evidence

ORD record
ord-1fc30808457f42e6ad8c7831359eebc2
Source dataset
uspto-grants-1990_12
Patent number
US04977159

Reaction notes

Loading…