Potassium Carbonate → HCID 9841532, compound

HRID 1278578Notes

Reaction equation

HRID 1278578 reaction equation
[CH2:1]([N:3]([CH2:32][CH3:33])[C:4]([C:6]1[CH:7]=[N:8][C:9]([C:12]2([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=3)[CH2:17][CH2:16][N:15](CC3C=CC=CC=3)[CH2:14][CH2:13]2)=[N:10][CH:11]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].ClC(OC(Cl)C)=O>ClCCCl>[CH2:32]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:7]=[N:8][C:9]([C:12]2([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=3)[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)=[N:10][CH:11]=1)=[O:5])[CH3:33]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5213051-Chloroethyl chloroformateHCID 70157241HCID 70157241, compound

Product 1

HCID 9841532HCID 9841532, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirring solution of 2-[1-Benzyl-4-(3-hydroxy-phenyl)-piperidin-4-yl]-pyrimidine-5-carboxylic acid diethylamide (105 mg, 0.24 mmol) in 5 mL 1,2-dichloroethane at room temperature was added potassium carbonate (K2CO3) (331 mg, 2.4 mmol) and 1-chloroethyl chloroformate (0.16 mL, 1.44 mmol). The mixture was refluxed for 24 hours, cooled to room temperature, filtered and concentrated. The resulting residue was taken up in 15 mL MeOH and refluxed for 24 hours. The mixture was cooled to room temperature and concentrated under reduced pressure to yield 86 mg (91%) of the desired amine. 1HNMR (400 MHz, CD3OD) δ 8.78 (s, 2H), 7.04 (t, 1H), 6.82-4.79 (comp, 2H), 6.54 (d, 1H), 3.55-3.32 (comp, 2H), 3.33-3.29 (comp, 2H), 2.99-2.93 (comp, 4H), 2.68 (t, 2H), 2.21 (t, 2H), 1.24-1.15 (comp, 6H); MS (M+1) 355.3

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. filtrationfiltered
  3. concentrationconcentrated
  4. temperaturerefluxed for 24 hours
  5. temperatureThe mixture was cooled to room temperature
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0f664b5260454d8aaba5b1adb9f6fdcf
Source dataset
uspto-grants-2002_09
Patent number
US06444679B1

Reaction notes

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