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

HRID 247310Notes

Reaction equation

HRID 247310 reaction equation
[Cl:1][CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=[S:12])[C:7]2[CH:13]=[CH:14][C:15]3[C:20]([C:6]=2[O:5]1)=[CH:19][CH:18]=[CH:17][CH:16]=3.[CH3:21][NH:22][CH3:23]>C(O)C>[ClH:1].[CH3:21][N:22]([CH3:23])[CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=[S:12])[C:7]2[CH:13]=[CH:14][C:15]3[C:20]([C:6]=2[O:5]1)=[CH:19][CH:18]=[CH:17][CH:16]=3

Participants

4

Reactant 2

HCID 674DimethylamineHCID 137263712-(2-Chloroethyl)-2,3-dihydro-4-methylnaphth[2,1-f][1,4]oxazepine-5(4H)-thione

Product 1

HCID 137263752-[2-(Dimethylamino)ethyl]-2,3-dihydro-4-methylnaphth [2,1-f][1,4]-oxazepine-5(4H)-thione hydrochlorideYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 15.0 g (0.05 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylnaphth[2,1-f][1,4]-oxazepine-5(4H)-thione in 50 ml of absolute ethanol was added 10 g of a 40% aqueous solution of dimethylamine. The resulting solution was heated in a steel bomb at 100° C. for 40 hr and concentrated under reduced pressure. The residue was partitioned between 15% aqueous sodium hydroxide and chloroform. The chloroform layer was evaporated and the residue partitioned between 3N hydrochloric acid and chloroform. The aqueous layer was made alkaline with 50% sodium hydroxide and extracted with chloroform. The chloroform extract was concentrated and the residue dissolved in isopropyl alcohol. Ethereal hydrogen chloride was added. Recrystallization of the precipitate from isopropyl alcohol/water gave 3.0 g (20%) of the product, m.p. 238°-240° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between 15% aqueous sodium hydroxide and chloroform
  3. customThe chloroform layer was evaporated
  4. customthe residue partitioned between 3N hydrochloric acid and chloroform
  5. extractionextracted with chloroform
  6. extractionThe chloroform extract
  7. concentrationwas concentrated
  8. dissolutionthe residue dissolved in isopropyl alcohol
  9. additionEthereal hydrogen chloride was added
  10. customRecrystallization of the precipitate from isopropyl alcohol/water

Sources & evidence

ORD record
ord-f340e641982842b3b176706c7e3ccca9
Source dataset
uspto-grants-1987_11
Patent number
US04705853

Reaction notes

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