Potassium Iodide → (R)-N-(2-((10,11-dihydro-5H-dibenzo [a, d]cyclohepten-5-ylidene)methoxy)ethyl)-3-piperidinecarboxylic acid ethyl ester

HRID 2226752Notes

Reaction equation

HRID 2226752 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][O:17][CH2:18][CH2:19]Br)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].C(C(C(C(O)=O)O)O)(O)=O.[NH:39]1[CH2:44][CH2:43][CH2:42][C@@H:41]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH2:40]1>CC(C)=O>[CH2:48]([O:47][C:45]([C@@H:41]1[CH2:42][CH2:43][CH2:44][N:39]([CH2:19][CH2:18][O:17][CH:16]=[C:6]2[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=3[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]2=3)[CH2:40]1)=[O:46])[CH3:49]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 2733695(R)-(-)-Ethyl Nipecotate TartrateHCID 109695372-((10, 11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)methoxy)ethylbromide

Product 1

HCID 11761301(R)-N-(2-((10,11-dihydro-5H-dibenzo [a, d]cyclohepten-5-ylidene)methoxy)ethyl)-3-piperidinecarboxylic acid ethyl esterYield 69.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-((10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)methoxy)ethylbromide (14.0 g, 42.5 mmol) in acetone (100 ml) was added potassium carbonate (23.5 g, 170 mmol), potassium iodide (0.7 g) and ethyl (R)-3-piperidinecarboxylate tartrate (19.6 g, 64 mmol). The suspension was stirred at room temperature for 3 days. The reaction mixture was filtered and the solvent was evaporated from the filtrate in vacuo. The oily residue was dissolved in ethyl acetate (150 ml). A 34% aqueous tartaric acid solution (100 ml) was added and pH was adjusted to 2.5 with a 4 M aqueous sodium hydroxide solution. The phases were separated and the organic phase was washed with a 2.5% aqueous solution of sodium bicarbonate (100 ml) and a 5% aqueous sodium bicarbonate solution (25 ml). The combined aqueous phases were extracted with ethyl acetate (100 ml). The combined organic phases were dried over magnesium sulphate. The solvent was evaporated in vacuo to give 12.0 g of (R)-N-(2-((10,11-dihydro-5H-dibenzo [a, d]cyclohepten-5-ylidene)methoxy)ethyl)-3-piperidinecarboxylic acid ethyl ester as an oil. TLC: rf=0.45 (SiO2 ; dichloromethane/methanol/acetic acid=20:2:1).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was evaporated from the filtrate in vacuo
  3. dissolutionThe oily residue was dissolved in ethyl acetate (150 ml)
  4. additionA 34% aqueous tartaric acid solution (100 ml) was added
  5. customThe phases were separated
  6. washthe organic phase was washed with a 2.5% aqueous solution of sodium bicarbonate (100 ml)
  7. extractionThe combined aqueous phases were extracted with ethyl acetate (100 ml)
  8. dry with materialThe combined organic phases were dried over magnesium sulphate
  9. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-48de774afc514c778464d4969945a3d6
Source dataset
uspto-grants-1994_09
Patent number
US05348965

Reaction notes

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