Triethylamine → HCID 54182534, compound

HRID 2082308Notes

Reaction equation

HRID 2082308 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([N:8]2[CH2:13][CH2:12][CH:11](C(O)=O)[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C([N:21]([CH2:24]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])C=CC=CC=1.[CH3:43][Si:44]([CH3:49])([CH3:48])[CH2:45][CH2:46][OH:47]>C1(C)C=CC=CC=1.C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[CH2:9][CH2:10][CH:11]([NH:21][C:24](=[O:33])[O:47][CH2:46][CH2:45][Si:44]([CH3:49])([CH3:48])[CH3:43])[CH2:12][CH2:13]2)=[O:7])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 180132-(Trimethylsilyl)ethanolHCID 199401P,P-Diphenylphosphinic azideHCID 7780751-(4-fluorobenzoyl)piperidine-4-carboxylic acid

Product 1

HCID 54182534HCID 54182534, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

1-(4-Fluorobenzoyl)piperidine-4-carboxylic acid (10.05 g, 40.0 mmol) and triethylamine (4.1 g, 40 mmol) are combined in toluene (50 mL) under a nitrogen atmosphere. Diphenylphosphoryl azide (11.0 g, 40.0 mmol) is added, and the mixture is heated at 80° C. for 2 hr. 2-(Trimethylsilyl)ethanol (9.49 g, 80.2 mmol) is added, and the mixture is stirred at 80° C. for 2 hr, and room temperature for 2 hr. The mixture is diluted with methylene chloride, washed twice with 1N HCl, twice with 0.5N sodium hydroxide, dried over magnesium sulfate, and evaporated. The residue is recrystallized from ether-hexane to afford the title compound.

Workup

  1. waitroom temperature for 2 hr
  2. washwashed twice with 1N HCl, twice with 0.5N sodium hydroxide
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue is recrystallized from ether-hexane

Sources & evidence

ORD record
ord-1568ae0940af4e3c963ce0b0fbaf6020
Source dataset
uspto-grants-1993_02
Patent number
US05189036

Reaction notes

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