4-Methylmorpholine → N-methoxy-N-methyloxane-4-carboxamide

HRID 588405Notes

Reaction equation

HRID 588405 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].CN1CCOCC1.[O:13]1[CH2:18][CH2:17][CH:16]([C:19](Cl)=[O:20])[CH2:15][CH2:14]1>C(Cl)Cl>[CH3:5][O:4][N:3]([CH3:2])[C:19]([CH:16]1[CH2:17][CH2:18][O:13][CH2:14][CH2:15]1)=[O:20]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2795505Oxane-4-carbonyl chloride

Product 1

HCID 23144693N-methoxy-N-methyloxane-4-carboxamideYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

N,O-Dimethylhydroxylamine hydrochloride (1.23 g, 12.7 mmol) and N-methylmorpholine (3.80 mL, 34.5 mmol) were dissolved in DCM (20 mL) and a solution of oxane-4-carbonyl chloride (1.71 g, 11.5 mmol) in DCM (20 mL) was added drop-wise. The reaction mixture was stirred for 2 h, then diluted to 200 mL with DCM, washed with 1 M aq HCl (2×100 mL), 1M aq Na2CO3 (100 mL) and water (100 mL), dried (MgSO4) and concentrated in vacuo to give the crude title compound as a yellow oil (1.87 g, 94%). LCMS (ES+): 174.1 (M+H)+.

Workup

  1. washwashed with 1 M aq HCl (2×100 mL), 1M aq Na2CO3 (100 mL) and water (100 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e6aa589740d54f7eb4defdf7c2d8a707
Source dataset
uspto-grants-2016_01
Patent number
US09227967B2

Reaction notes

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