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

HRID 1416894Notes

Reaction equation

HRID 1416894 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

Conditions

Temperature
65 °C

Procedure

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. customprepared
  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-0f1bce6ca5bf42afa4c449dd314d2a27
Source dataset
uspto-grants-1999_06
Patent number
US05916901

Reaction notes

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