2-Chloro-N,N-dimethylethylamine → HCID 131716783, compound

HRID 981471Notes

Reaction equation

HRID 981471 reaction equation
[C:1]([O:4][C@H:5]1[C@H:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[S:10][CH:9]=[C:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[NH:7][C:6]1=[O:26])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:33][N:34]([CH3:38])[CH2:35][CH2:36]Cl>C(OCC)(=O)C.O>[C:1]([O:4][C@H:5]1[C@H:11]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[S:10][CH:9]=[C:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:7]([CH2:36][CH2:35][N:34]([CH3:38])[CH3:33])[C:6]1=[O:26])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamine2×HCID 11430Potassium CarbonateHCID 131716784HCID 131716784, compound

Product 1

HCID 131716783HCID 131716783, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.1 g (0.003 mol) of rac.-trans-6-(acetyloxy)-6,7-dihydro-7-(4-methoxyphenyl) -3-phenyl-1,4-thiazepin-5(4H)-one, 0.5 g of potassium carbonate (powdered) and 0.3 g (0.003 mol) of 2-dimethylaminoethyl chloride in 25 mL of ethyl acetate was stirred and heated at reflux for 2 hrs, then twice an additional 0.15 g of 2-dimethylaminoethyl chloride was added at 2 hr intervals. The mixture was heated at reflux for a total of 12 hrs., cooled to room temperature and diluted with water. The aqueous suspension was extracted with ethyl acetate then the organic solution was washed with brine and dried (MgSO4). Removal of the solvent gave 1.2 g (92%) of rac.-trans-6-(acetyloxy)-6,7-dihydro-7-(4-methoxyphenyl) -4-[2-(dimethylamino)ethyl]-3-phenyl-1,4-thiazepin-5(4H) -one. Analytical sample was recrystallized from ether, mp 147°-148°.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hrs
  3. temperatureThe mixture was heated
  4. temperatureat reflux for a total of 12 hrs
  5. extractionThe aqueous suspension was extracted with ethyl acetate
  6. washthe organic solution was washed with brine
  7. dry with materialdried (MgSO4)
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-84e30bc19c224f15b79bad767211892a
Source dataset
uspto-grants-1991_02
Patent number
US04992432

Reaction notes

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