Morpholine → 2,3-Dihydro-4-methyl-2-[2-(4-morpholinyl)ethyl]pyrido[3,2-f][1,4]oxazepin-5(4H)-thione

HRID 4840Notes

Reaction equation

HRID 4840 reaction equation
Cl[CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=[S:12])[C:7]2[CH:13]=[CH:14][CH:15]=[N:16][C:6]=2[O:5]1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>>[CH3:11][N:9]1[C:8](=[S:12])[C:7]2[CH:13]=[CH:14][CH:15]=[N:16][C:6]=2[O:5][CH:4]([CH2:3][CH2:2][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH2:10]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 137264422-(chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)thione

Product 1

HCID 137264902,3-Dihydro-4-methyl-2-[2-(4-morpholinyl)ethyl]pyrido[3,2-f][1,4]oxazepin-5(4H)-thione

Procedure

2-(2-Chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-thione, 4.5 g (0.018 mole) was dissolved in morpholine (30 ml). The solution was heated with stirring to 50°-60° C. for 6 hr. The morpholine was then removed by rotary evaporation (90° C., vacuum pump). The residue was taken up in chloroform (100 ml) and washed with dilute aqueous sodium hydroxide (2×30 ml). The organic layer was concentrated by rotary evaporation (60° C., water aspirator). The residue was recrystallized from ethanol giving 3.26 g (60%) of light yellow crystals, m.p. 152°-153° C.

Workup

  1. temperatureThe solution was heated
  2. customThe morpholine was then removed by rotary evaporation (90° C., vacuum pump)
  3. washwashed with dilute aqueous sodium hydroxide (2×30 ml)
  4. concentrationThe organic layer was concentrated by rotary evaporation (60° C., water aspirator)
  5. customThe residue was recrystallized from ethanol giving 3.26 g (60%) of light yellow crystals, m.p. 152°-153° C.

Sources & evidence

ORD record
ord-db521c60394943f7aa9b07de7bbb410c
Source dataset
uspto-grants-1988_02
Patent number
US04727152

Reaction notes

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