4-Methylmorpholine → N-Methoxy-N-methyl-4-fluoro-benzenepropanamide

HRID 1592349Notes

Reaction equation

HRID 1592349 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.CN1CCOCC1.C(OC(Cl)=O)C(C)C.Cl.[CH3:29][NH:30][O:31][CH3:32]>C1COCC1.C1COCC1.O.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([N:30]([O:31][CH3:32])[CH3:29])=[O:12])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 1363023-(4-Fluorophenyl)propionic acid

Product 1

HCID 22612404N-Methoxy-N-methyl-4-fluoro-benzenepropanamideYield 97.8%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 3-(4-fluorophenyl)propanoic acid (5.0 g, 30 mmol) in THF is cooled in an ice bath and treated with N-methyl morpholine (NMM) (3.0 g, 30 mmol), isobutylchloroformate (4.04 g, 30 mmol) and stirred for few mins. This was then treated with a solution of N,O-Dimethyl hydroxylamine hydrochloride (3.0 g, 30 mmol) in THF/water (neutralized with 3.0 g of NMM) and stirred for 30 minutes. The reaction mixture is diluted with CH2Cl2 and washed successively with 1 N NaOH, water and brine. The solvent was evaporated under vacuum to give 6.2 g of 3-(4-fluorophenyl)-N-methoxy-N-methylpropanamide as oil.

Workup

  1. stirringstirred for 30 minutes
  2. washwashed successively with 1 N NaOH, water and brine
  3. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-4c79be0f979d49a38b7d738070a0552e
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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