Dimethylamine → 2-[2-(Dimethylamino)ethyl]-2,3-dihydro-2,4-dimethylpyrido[3,2-f][1,4]oxazepin-5(4H)-one dihydrochloride

HRID 364426Notes

Reaction equation

HRID 364426 reaction equation
[ClH:1].[Cl:2][CH2:3][CH2:4][C:5]1([CH3:18])[CH2:11][N:10]([CH3:12])[C:9](=[O:13])[C:8]2[CH:14]=[CH:15][CH:16]=[N:17][C:7]=2[O:6]1.[CH3:19][NH:20][CH3:21]>CO>[ClH:2].[ClH:1].[CH3:19][N:20]([CH3:21])[CH2:3][CH2:4][C:5]1([CH3:18])[CH2:11][N:10]([CH3:12])[C:9](=[O:13])[C:8]2[CH:14]=[CH:15][CH:16]=[N:17][C:7]=2[O:6]1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 137264722-(2-Chloroethyl)-2,3-dihydro-2,4-dimethylpyrido[3,2-f]-1,4-oxazepin-5(4H)-one hydrochloride

Product 1

HCID 137266322-[2-(Dimethylamino)ethyl]-2,3-dihydro-2,4-dimethylpyrido[3,2-f][1,4]oxazepin-5(4H)-one dihydrochlorideYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 4.5 g (0.015 mole) of 2-(2-chloroethyl)-2,3-dihydro-2,4-dimethylpyrido[3,2-f]-1,4-oxazepin-5(4H)-one hydrochloride in 15 ml of methanol was added 40 ml of dimethylamine. The flask was sealed tightly and left standing at room temperature for 8 days. The methanol and dimethylamine were removed by rotary evaporation (70° C.; 30 mm). The residue was taken up in 150 ml of chloroform, washed with 2×50 ml dil aqueous sodium hydroxide, dried over anhydrous sodium sulfate, filtered and concentrated by rotary evaporation (70° C.; 30 mm). The syrupy residue was treated with hydrogen chloride in isopropyl alcohol, which afforded 3.5 g (67%) of white crystals, m.p. 188°-90° C.

Workup

  1. customThe flask was sealed tightly
  2. waitleft
  3. customThe methanol and dimethylamine were removed by rotary evaporation (70° C.; 30 mm)
  4. washwashed with 2×50 ml dil aqueous sodium hydroxide
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation (70° C.; 30 mm)
  8. additionThe syrupy residue was treated with hydrogen chloride in isopropyl alcohol, which

Sources & evidence

ORD record
ord-11141d89bfc24efb8e0e6ec0832c614c
Source dataset
uspto-grants-1986_08
Patent number
US04604388

Reaction notes

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