Methanol → HCID 18919559, compound

HRID 1290880Notes

Reaction equation

HRID 1290880 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].C(OC(=O)C[N:12]1[CH2:17][CH2:16][C:15](=[C:18]2[C:24]3=[N:25][CH:26]=[CH:27][CH:28]=[C:23]3[CH2:22][CH2:21][C:20]3[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:19]2=3)[CH2:14][CH2:13]1)C.[CH3:35]O>>[Cl:33][C:30]1[CH:31]=[CH:32][C:19]2[C:18](=[C:15]3[CH2:14][CH2:13][N:12]([CH:1]([OH:4])[CH3:35])[CH2:17][CH2:16]3)[C:24]3=[N:25][CH:26]=[CH:27][CH:28]=[C:23]3[CH2:22][CH2:21][C:20]=2[CH:29]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 14554136HCID 14554136, compound

Product 1

HCID 18919559HCID 18919559, compoundYield 71%

Procedure

An aqueous solution of potassium carbonate (299 mg, 2.16 mmol, 5 ml water) was added to a solution of ethyl-(4-{8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta-[ 1,2- b]pyridin-11-ylidene)piperidin-1-yl)acetate (214 mg, 0.54 mmol) in methanol (20 ml). The reaction was stirred at room temperature for 24 hours followed by 3 hours at 800° C. Methanol was removed under reduced pressure and the residue partitioned between DCM and brine. The crude product was purified by chromatography on silica gel using a gradient elution of 5% methanol in DCM. Product containing fractions were combined and solvent evaporated to leave 4-{8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene}-piperidin-1-yl-ethanol as a white solid (136 mg, 71%).

Workup

  1. waitfollowed by 3 hours at 800° C
  2. customMethanol was removed under reduced pressure
  3. customthe residue partitioned between DCM and brine
  4. customThe crude product was purified by chromatography on silica gel using
  5. washa gradient elution of 5% methanol in DCM
  6. additionProduct containing fractions
  7. customsolvent evaporated

Sources & evidence

ORD record
ord-00c85136dd944adda641f86d25f915e2
Source dataset
uspto-grants-1998_05
Patent number
US05753671

Reaction notes

Loading…