Potassium Carbonate → HCID 86615507, compound

HRID 253085Notes

Reaction equation

HRID 253085 reaction equation
C([N:8]1[CH2:13][C:12]([CH2:14][O:15][CH2:16][C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=2)=[C:11]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[CH3:37])[CH2:10][CH2:9]1)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[Cl:44]C(OC(Cl)C)=O>ClCCCl>[ClH:44].[F:25][C:23]([F:24])([F:26])[C:21]1[CH:22]=[C:17]([CH:18]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:20]=1)[CH2:16][O:15][CH2:14][C:12]1[CH2:13][NH:8][CH2:9][CH2:10][C:11]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH3:37]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5213051-Chloroethyl chloroformateHCID 24752610HCID 24752610, compound

Product 1

HCID 86615507HCID 86615507, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1-benzyl-5-(3,5-bis-trifluoromethyl-benzyloxymethyl)-4-o-tolyl-1,2,3,6-tetrahydro-pyridine (76 mg, 0.15 mmol), potassium carbonate (20 mg, 0.15 mmol) and 1-chloroethyl chloroformate (23 mg, 0.16 mmol) in 3 ml of 1,2-dichloroethane was heated at 50° C. for 3 h. The mixture was filtered and concentrated in vacuo. The residue was dissolved in 2 ml of methanol and heated at reflux over night. Evaporation of the solvent in vacuo was followed by flash column chromatography to give the free base of the title compound. Dissolution in a 2 M solution of hydrochloric acid in diethyl ether and concentration in vacuo gave 57 mg (84%) of the title compound as a white solid.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in 2 ml of methanol
  4. temperatureheated
  5. temperatureat reflux over night
  6. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-01cf4fa0cc0e4ae7b0584a86010d663c
Source dataset
uspto-grants-2011_01
Patent number
US07872022B2

Reaction notes

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