Potassium Carbonate → HCID 10906240, compound

HRID 2226755Notes

Reaction equation

HRID 2226755 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[N:6]([CH2:16][CH2:17][CH2:18][OH:19])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:20]([Li])[CH2:21]CC.CS(Cl)(=O)=O.[NH:30]1[CH2:35][CH2:34][CH2:33][C@@H:32]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:31]1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.CC(C)=O>[CH2:39]([O:38][C:36]([C@@H:32]1[CH2:33][CH2:34][CH2:35][N:30]([CH2:20][CH2:21][O:19][CH2:18][CH2:17][CH2:16][N:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][CH2:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=3)[CH2:31]1)=[O:37])[CH3:40]

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 185582ethyl (3R)-piperidine-3-carboxylateHCID 110214143-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propanolHCID 178418339Butyllithium

Product 1

HCID 10906240HCID 10906240, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

A solution of the above alcohol (0.60 g, 2.0 mmol) in dry THF (15 ml) was placed under an atmosphere of nitrogen and then cooled on an ice-bath. A solution of n-butyllithium in hexanes (0.88 ml, 2.5 M) was added dropwise at 10° C. When addition was complete the mixture was stirred at 10° C. for 30 minutes. Methanesulfonyl chloride (0.25 g, 2.2 mmol) was added and the reaction mixture was stirred at room temperature for 90 minutes. The volatiles were evaporated in vacuo leaving a residue which was dissolved in acetone (20 ml). Ethyl (R)-3-piperidinecarboxylate (0.50 g, 3.0 mmol) and potassium carbonate (0.7 g, 5 mmol) were added and the suspension was stirred at room temperature for 16 h and the heated at reflux temperature for 7 h. The cooled reaction mixture was filtered and the solvent was evaporated in vacuo. The oily residue was submitted to column chromatography on silica gel (150 g) using a mixture of ethyl acetate and n-heptane (2:3) as eluent. Collecting the proper fractions afforded 0.4 g of (R)-N-(2((3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propyl)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester as an oil.

Workup

  1. temperaturecooled on an ice-bath
  2. additionWhen addition
  3. stirringthe reaction mixture was stirred at room temperature for 90 minutes
  4. customThe volatiles were evaporated in vacuo
  5. customleaving a residue which
  6. stirringthe suspension was stirred at room temperature for 16 h
  7. temperaturethe heated
  8. temperatureat reflux temperature for 7 h
  9. customThe cooled reaction mixture
  10. filtrationwas filtered
  11. customthe solvent was evaporated in vacuo
  12. additiona mixture of ethyl acetate and n-heptane (2:3) as eluent
  13. customCollecting the proper fractions

Sources & evidence

ORD record
ord-cf0df5d1c6e94f3885c477b5dc6af492
Source dataset
uspto-grants-1994_09
Patent number
US05348965

Reaction notes

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