Methylamine → 1-(6-Benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-3-methylamino-propan-1-one

HRID 2224072Notes

Reaction equation

HRID 2224072 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:18][CH2:17][CH2:16][N:15]([C:19](=[O:23])[CH2:20][CH2:21]Cl)[C:14]=3[CH:24]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:25][CH3:26]>>[C:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:18][CH2:17][CH2:16][N:15]([C:19](=[O:23])[CH2:20][CH2:21][NH:25][CH3:26])[C:14]=3[CH:24]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 586415551-(6-Benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-3-chloro-propan-1-one

Product 1

HCID 586415371-(6-Benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-3-methylamino-propan-1-oneYield 93%

Procedure

A solution of 1-(6-benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-3-chloro-propan-1-one (0.100 g., 0.273 mmol) in 4 mL of 2 M methanolic H2NMe was heated in a microwave reactor in a sealed reaction vessel at 80° C. for 2 minutes, then at 130° C. for 8 minutes. The reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography (24:1:0.1 of CH2Cl2:MeOH:NH4OH) to give 0.092 g (93%) of 1-(6-benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-3-methylamino-propan-1-one as a clear oil. MS: 361 (M+H)+, mp: 208.3-214.7° C. (as hydrochloride).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by flash chromatography (24:1:0.1 of CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-93012721389c4dd3a05512f1d69dc55f
Source dataset
uspto-grants-2008_05
Patent number
US07378415B2

Reaction notes

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