Dimethylamine → 2-[2-(Dimethylamino)ethyl]-2,3-dihydro-2,4-dimethylpyrido[3,2-f][1,4]oxazepine-5(4H)-thione monohydrochloride

HRID 1194243Notes

Reaction equation

HRID 1194243 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1([CH3:17])[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.[CH3:18][NH:19][CH3:20]>CO>[ClH:1].[CH3:18][N:19]([CH3:20])[CH2:2][CH2:3][C:4]1([CH3:17])[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

Participants

4

Reactant 2

HCID 674DimethylamineHCID 137264732-(2-chloroethyl)-2,3-dihydro-2,4-dimethylpyrido[3,2-f]-1,4-oxazepine-5(4H)-thione

Product 1

HCID 137266342-[2-(Dimethylamino)ethyl]-2,3-dihydro-2,4-dimethylpyrido[3,2-f][1,4]oxazepine-5(4H)-thione monohydrochlorideYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 4.5 g (0.017 mole) of 2-(2-chloroethyl)-2,3-dihydro-2,4-dimethylpyrido[3,2-f]-1,4-oxazepine-5(4H)-thione in 20 ml of methanol, cooled in an ice bath, was added 40 ml of dimethylamine. The flask was sealed tightly and left standing at room temperature for 10 days. the dimethylamine and methanol were removed by rotary evaporation (60° C.; 30 mm). The residue was taken up in 150 ml of chloroform, washed with 3×50 ml dil sodium hydroxide, dried over anhydrous sodium sulfate, filtered and concentrated by rotary evaporation (70° C.; 30 mm). The crude oil was dissolved in isopropyl alcohol and treated with ethereal hydrogen chloride, which yielded 4.0 g (76%) of yellow crystals, m.p. 255° C. with decomposition.

Workup

  1. temperaturecooled in an ice bath
  2. customThe flask was sealed tightly
  3. waitleft
  4. customthe dimethylamine and methanol were removed by rotary evaporation (60° C.; 30 mm)
  5. washwashed with 3×50 ml dil sodium hydroxide
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation (70° C.; 30 mm)
  9. dissolutionThe crude oil was dissolved in isopropyl alcohol
  10. additiontreated with ethereal hydrogen chloride, which

Sources & evidence

ORD record
ord-30ff9370742a46d883645ec09b6af645
Source dataset
uspto-grants-1989_03
Patent number
US04812565

Reaction notes

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