Triethylamine → HCID 9798021, compound

HRID 1836355Notes

Reaction equation

HRID 1836355 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:13]=[C:14]([CH:24]=[CH:25][CH:26]=1)[C:15]([CH:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1)=[O:16].C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C.[OH-].[Na+]>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:11][C:12]2[CH:13]=[C:14]([CH:24]=[CH:25][CH:26]=2)[C:15]([CH:17]2[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22]2)=[O:16])=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 101306514-[3-Aminobenzoyl]-1-methylpiperidine

Product 1

HCID 9798021HCID 9798021, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-Fluorobenzoyl chloride (0.98 ml, 8.3 mmol) was added dropwise to a 0° C. solution of 4-[3-aminobenzoyl]-1-methylpiperidine (1.64 g, 7.5 mmol) and triethylamine (1.3 ml, 9.0 mmol) in tetrahydrofuran (20 ml). The reaction mixture stirred 2 h at room temperature, diluted with ethyl acetate and 1N sodium hydroxide solution and extracted with ethyl acetate. The ethyl acetate extracts were washed with water, brine, then dried over sodium sulfate. Solvent was removed under reduced pressure to give 2.5 g (98%) of a foam.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate extracts were washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a2cc6713cd4049feb31be5393ad67ed2
Source dataset
uspto-grants-2004_08
Patent number
US06777428B1

Reaction notes

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