Triethylamine → HCID 86759276, compound

HRID 431068Notes

Reaction equation

HRID 431068 reaction equation
[CH:1]1([O:6][C:7]2[C:12]([O:13][CH3:14])=[CH:11][N:10]=[C:9]([CH2:15][CH2:16][NH2:17])[CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:25](Cl)(=[O:33])[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[CH:1]1([O:6][C:7]2[C:12]([O:13][CH3:14])=[CH:11][N:10]=[C:9]([CH2:15][CH2:16][NH:17][C:25](=[O:33])[O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 18763372HCID 18763372, compound

Product 1

HCID 86759276HCID 86759276, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

A mixture of 4-(cyclopentyloxy)-5-methoxy-2-pyridineethanamine (0.026 mol) and triethylamine (0.03 mol) in CH2Cl2 (75ml) was stirred at 0-5° C. A mixture of phenyl carbonochloridate (0.03 mol) in CH2Cl2 (25ml) was added dropwise. The mixture was stirred at RT for 1 hour and then washed with NaOH (1N) and water. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified over silica gel on a glass filter (eluent: CH2Cl2/CH3OH 98/2). The pure fractions were collected and the solvent was evaporated. The residue was dried, yielding 7.2g (77.7%) of phenyl [2-[4-(cyclopentyloxy)-5-methoxy-2-pyridinyl]ethyl]carbamate (interm. 3).

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred at RT for 1 hour
  3. washwashed with NaOH (1N) and water
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified over silica gel on a glass
  9. filtrationfilter (eluent: CH2Cl2/CH3OH 98/2)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated
  12. customThe residue was dried

Sources & evidence

ORD record
ord-47b2da6de30a4a31b8e5d3c791d2ee8b
Source dataset
uspto-grants-2003_12
Patent number
US06656959B1

Reaction notes

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