4-Methylmorpholine → Methyl 3(6-Hexanamido-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl)benzoate

HRID 1646367Notes

Reaction equation

HRID 1646367 reaction equation
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:9][C:10]1[CH:11]=[CH:12][C:13]2[O:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]3[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=3)[C:23]([O:25][CH3:26])=[O:24])[C:14]=2[CH:30]=1.CN1CCOCC1>ClCCl>[C:1]([NH:9][C:10]1[CH:11]=[CH:12][C:13]2[O:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]3[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=3)[C:23]([O:25][CH3:26])=[O:24])[C:14]=2[CH:30]=1)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 67340Hexanoyl chlorideHCID 54048005Methyl 3-(6-amino-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl)benzoate

Product 1

HCID 23365863Methyl 3(6-Hexanamido-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Hexanoyl chloride (0.135 g.) was added dropwise to a stirred solution of methyl 3-(6-amino-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl)benzoate (X) (0.3 g.), and N-methylmorpholine (0.101 g.) in dichloromethane (30 ml.). After 0.5 hours, the mixture was diluted with dichloromethane, washed with water, dried (MgSO4) and evaporated to give an oil which was filtered through a short column of silica gel using 35:65 v/v ethyl acetate:hexane to give the title compound as a syrup: partial NMR (80 MHz, CDCl3): 0.8-1.9 [complex m,9 H, CH3 (CH2)3 ]; 2.2 (m,2 H, CH2CONH); 3.3 (m,2 H, N.CH2.CH2.O; 3.9 (s,3 H, OMe); 4.2 (m,2 H, N.CH2.CH2O); 4.5 (s,2 H, N.CH2Ar).

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customto give an oil which
  5. filtrationwas filtered through a short column of silica gel using 35:65 v/v ethyl acetate

Sources & evidence

ORD record
ord-ea77bdbe8bca42c69f1d812079962161
Source dataset
uspto-grants-1993_01
Patent number
US05179112

Reaction notes

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