4-Methylmorpholine → HCID 89815860, compound

HRID 1487130Notes

Reaction equation

HRID 1487130 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=O)([O-:3])=[O:2].CN1CCOCC1.ClC(OCC)=O.[O:26]1[CH2:31][CH2:30][CH:29]([NH2:32])[CH2:28][CH2:27]1>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([NH:32][CH:29]1[CH2:30][CH2:31][O:26][CH2:27][CH2:28]1)=[O:9])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 84973-Nitrobenzoic acidHCID 10928Ethyl chloroformateHCID 4192234-Aminotetrahydropyran

Product 1

HCID 89815860HCID 89815860, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under nitrogen atmosphere, 3-nitrobenzoic acid (1.00 g, 5.98 mmol) was taken in THF (20 ml) and the mixture was cooled to 0° C. followed by addition of N-methylmorpholine (0.85 ml, 7.78 mmol) and ethyl chloroformate (6.58 mmol). The reaction mixture was stirred for 30 min at 0° C. and tetrahydro-2H-pyran-4-amine (0.6 ml, 5.98 mmol) was added and the reaction mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated under vacuum and the residue was taken in ethyl acetate (20 ml), washed with water and brine, dried over sodium sulfate and concentrated under vacuum to afford the solid product (1.2 gm).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 30 min
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a100a3527d484c698c44048527057c59
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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