Sodium Iodide → 1-(3-(12H-dibenzo[d,g][1,3]dioxocin-12-ylidene)-1-propyl)-4-piperidinecarboxylic acid ethyl ester

HRID 1291032Notes

Reaction equation

HRID 1291032 reaction equation
Br[CH2:2][CH2:3][CH:4]=[C:5]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH2:9][O:8][C:7]2[CH:17]=[CH:18][CH:19]=[CH:20][C:6]1=2.[CH2:21]([O:23][C:24]([CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=[O:25])[CH3:22].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[CH2:21]([O:23][C:24]([CH:26]1[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][CH:4]=[C:5]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[O:10][CH2:9][O:8][C:7]3[CH:17]=[CH:18][CH:19]=[CH:20][C:6]2=3)[CH2:28][CH2:27]1)=[O:25])[CH3:22]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 70770Ethyl 4-piperidinecarboxylateHCID 17127115-(3-Bromopropylidene)benzo[d][1,3]benzodioxocine

Product 1

HCID 508523541-(3-(12H-dibenzo[d,g][1,3]dioxocin-12-ylidene)-1-propyl)-4-piperidinecarboxylic acid ethyl esterYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(3-(12H-Dibenzo[d,g][1,3]dioxocin-12-ylidene)-1-propyl)-4-pipenrdinecaboxylic acid hydrochloride ##STR6## A mixture of 12-(3-bromo-1-propylidene)-12H-dibenzo[d,g][1,3]dioxocine (4.0 g, 12 mmol, prepared as described in example 1), 4-piperidinecarboxylic acid ethyl ester (1.9 g, 12 mmol), anhydrous potassium carbonate (5.0 g) and sodium iodide (0.2 g) in N,N-dimethylformamide (40 ml) was heated at 60°-70° C. for 5 h. After cooling, the inorganic salts were filtered off and washed with benzene (40 ml), and the filtrate was diluted with additional benzene (120 ml). The benzene solution was washed with water (3×50 ml), dried over MgSO4 and evaporated in vacuo. The oily residue (4.8 g) was purified by chromatography on silica gel using a mixture of benzene and ethyl acetate as eluent to give 1-(3-(12H-dibenzo[d,g][1,3]dioxocin-12-ylidene)-1-propyl)4-piperidinecarboxylic acid ethyl ester as an oil (2.3 g, 47%).

Workup

  1. temperaturewas heated at 60°-70° C. for 5 h
  2. temperatureAfter cooling
  3. filtrationthe inorganic salts were filtered off
  4. washwashed with benzene (40 ml)
  5. additionthe filtrate was diluted with additional benzene (120 ml)
  6. washThe benzene solution was washed with water (3×50 ml)
  7. dry with materialdried over MgSO4
  8. customevaporated in vacuo
  9. customThe oily residue (4.8 g) was purified by chromatography on silica gel using
  10. additiona mixture of benzene and ethyl acetate as eluent

Sources & evidence

ORD record
ord-5846db6c5db2498db54455568105ca25
Source dataset
uspto-grants-1998_05
Patent number
US05753678

Reaction notes

Loading…