Pyridine → HCID 58495732, compound

HRID 2359356Notes

Reaction equation

HRID 2359356 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][CH2:4]1.N1C=CC=CC=1.Cl[C:26](OC1C=CC([N+]([O-])=O)=CC=1)=[O:27].Cl.[CH3:39][NH:40][CH:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1.C(N(CC)CC)C>ClCCl.O>[CH3:39][N:40]([CH:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1)[C:26]([O:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH2:5][CH2:4]1)=[O:27]

Participants

8

Reactant 5

HCID 1049PyridineHCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 736490Benzyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 22736998N-methyloxan-4-amine hydrochloride

Product 1

HCID 58495732HCID 58495732, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate (2.14 g, 8.57 mmol) was dissolved in dichloromethane (26 mL), to which pyridine (1.04 mL, 12.9 mmol) and p-nitrophenyl chloroformate (2.07 g, 12.9 mmol) were added, followed by stirring at room temperature for 35 minutes under a nitrogen atmosphere. Subsequently, N-methyltetrahydro-2H-pyran-4-amine hydrochloride (1.30 g, 8.57 mmol) and triethylamine (3.59 mL, 25.7 mmol) were added, followed by further stirring for 4.5 hours. Water was added to the resulting reaction liquid, and the resulting mixture was extracted with dichloromethane. The resulting organic layer was dried over sodium sulfate and the solvent was distilled off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-50:50, V/V) to give the desired title compound (2.22 g, yield 66%).

Workup

  1. additionwere added
  2. stirringby further stirring for 4.5 hours
  3. extractionthe resulting mixture was extracted with dichloromethane
  4. dry with materialThe resulting organic layer was dried over sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-50:50, V/V)

Sources & evidence

ORD record
ord-ededb4464b2c4db9a6fc5c9e5343bb9f
Source dataset
uspto-grants-2014_04
Patent number
US08685981B2

Reaction notes

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