Triethylamine → HCID 131724525, compound

HRID 1836356Notes

Reaction equation

HRID 1836356 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1C([Cl:8])=O.[NH2:9][C:10]1[CH:11]=[C:12]([CH:22]=[CH:23][CH:24]=1)[C:13]([CH:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1)=[O:14].C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C.[OH-].[Na+]>[ClH:8].[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[N-:9][C:10]1[CH:11]=[C:12]([CH:22]=[CH:23][CH:24]=1)[C:13]([CH:15]1[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]1)=[O:14]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 101306514-[3-Aminobenzoyl]-1-methylpiperidine

Product 1

HCID 131724525HCID 131724525, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-Furoyl chloride (0.15 ml, 1.5 mmol) was added to a solution of 4-[3-aminobenzoyl]-1-methylpiperidine (257 mg, 1.2 mmol) and triethylamine (0.2 ml, 1.4 mmol) in tetrahydrofuran (10 ml). The reaction mixture was stirred 2 h at room temperature. The reaction mixture was diluted with ethyl acetate and 1N sodium hydroxide then extracted with ethyl acetate. The ethyl acetate extracts were washed with 1N sodium hydroxide, water, brine, then dried over sodium sulfate. The solvent was removed under reduced pressure to give 440 mg. Purification by radial chromatography (silica gel, 2000 micron rotor, methylene chloride:methanol:ammonium hydroxide, 100:5:0.5) gave 350 mg (95%) of a foam. Crystallization as the hydrochloric acid salt from ethyl acetate/ethanol provided 320 mg of a yellow powder with mp>200° C. MS(m/e): 313(M+1), 311(M−1).

Workup

  1. extractionthen extracted with ethyl acetate
  2. washThe ethyl acetate extracts were washed with 1N sodium hydroxide, water, brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customto give 440 mg
  6. customPurification by radial chromatography (silica gel, 2000 micron rotor, methylene chloride:methanol:ammonium hydroxide, 100:5:0.5)

Sources & evidence

ORD record
ord-66ee582dd1d74d78aa301fb5e6b299d7
Source dataset
uspto-grants-2004_08
Patent number
US06777428B1

Reaction notes

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