Hydrochloric Acid → HCID 69946532, compound

HRID 1276410Notes

Reaction equation

HRID 1276410 reaction equation
Br[CH2:2][CH2:3][CH:4]=[C:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:28]([O:30][C:31]([CH:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)=[O:32])[CH3:29].[ClH:39]>C(C(C)=O)C.C(OCC)(=O)C.O>[ClH:39].[CH2:28]([O:30][C:31]([CH:33]1[CH2:38][CH2:37][N:36]([CH2:2][CH2:3][CH:4]=[C:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[CH2:9][CH2:8][C:7]3[CH:16]=[CH:17][CH:18]=[CH:19][C:6]2=3)[CH2:35][CH2:34]1)=[O:32])[CH3:29]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 70770Ethyl 4-piperidinecarboxylateHCID 17126855-(3-bromopropylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Product 1

HCID 69946532HCID 69946532, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(3-Bromo-1-propylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (3.00 g, 0.0096 mol), potassium carbonate (8.3 g, 0.060 mol), potassium iodide (3.3 g, 0.020 mol) and 4-piperidinecarboxylic acid ethyl ester (3.1 ml, 0.020 mol) was mixed in methyl ethyl ketone (100 ml) and heated at reflux temperature for 20 h and stirred at room temperature for 3 days. Water (100 ml) was added, the phases were separated, and the aqueous phase was extracted with ethyl acetate. The organic phase was dried (MgSO4) and evaporated in vacuo to give the crude product in almost quantitative yield. The crude product was treated with 1 N hydrochloric acid and ethyl acetate, evaporated to dryness and crystallised from ethyl acetate to give 2.89 g of 1-(3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propyl)4-piperidinecarboxylic acid ethyl ester hydrochloride as a solid.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 20 h
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated in vacuo
  7. customto give the crude product in almost quantitative yield
  8. customevaporated to dryness
  9. customcrystallised from ethyl acetate

Sources & evidence

ORD record
ord-af7f478e882b4ca9bf1c74bc1e496df0
Source dataset
uspto-grants-2000_12
Patent number
US06166009

Reaction notes

Loading…