Dimethylamine → 2-[2-(Dimethylamino)ethyl]-2,3-dihydro-4,8-dimethylpyrido[3,2-f][1,4]-oxazepin-5(4H)-one fumarate

HRID 4866Notes

Reaction equation

HRID 4866 reaction equation
[CH3:1][NH:2][CH3:3].O.Cl[CH2:6][CH2:7][CH:8]1[CH2:14][N:13]([CH3:15])[C:12](=[O:16])[C:11]2[CH:17]=[CH:18][C:19]([CH3:21])=[N:20][C:10]=2[O:9]1.[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26]>C(O)(C)C>[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26].[CH3:1][N:2]([CH3:3])[CH2:6][CH2:7][CH:8]1[CH2:14][N:13]([CH3:15])[C:12](=[O:16])[C:11]2[CH:17]=[CH:18][C:19]([CH3:21])=[N:20][C:10]=2[O:9]1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 444972Fumaric AcidHCID 13726454HCID 13726454, compound

Product 1

HCID 212714462-[2-(Dimethylamino)ethyl]-2,3-dihydro-4,8-dimethylpyrido[3,2-f][1,4]-oxazepin-5(4H)-one fumarate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To 50 ml of freshly collected dimethylamine was added 5.0 g (0.020 mole) of 2-(2-chloroethyl)-2,3-dihydro-4,8-dimethylpyrido[3,2-f]-1,4-oxazepin-5(4H)-one hydrate [1:1]. The reaction flask was sealed tightly and left standing at room temperature for 3 days. The dimethylamine was evaporated in a stream of air. The residue was taken up in methylene chloride, washed twice with 1N sodium hydroxide and once with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. The syrupy residue was treated with 2 equivalents of fumaric acid in isopropyl alcohol which yield 5.2 g (52%) of white crystals, m.p. 164°-165° C.

Workup

  1. customThe reaction flask was sealed tightly
  2. waitleft
  3. customThe dimethylamine was evaporated in a stream of air
  4. washwashed twice with 1N sodium hydroxide and once with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-ba780da7ad95459898e6dbacd6e9e38a
Source dataset
uspto-grants-1988_02
Patent number
US04727152

Reaction notes

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