2-Chloro-N,N-dimethylethylamine → HCID 70083343, compound

HRID 981468Notes

Reaction equation

HRID 981468 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]=[CH:8][NH:7][C:6]1=[O:20])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30][Cl:31]>C(OCC)(=O)C.O>[ClH:31].[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:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:7]([CH2:30][CH2:29][N:28]([CH3:32])[CH3:27])[C:6]1=[O:20])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamine2×HCID 11430Potassium CarbonateHCID 131716782HCID 131716782, compound

Product 1

HCID 70083343HCID 70083343, compoundYield 167.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3.9 g (0.01 mol) of rac.-cis-6-(acetyloxy)-6,7-dihydro-7-(4-methoxyphenyl)-1, 4-thiazepin-5(4H)-one, 1.5 g of powdered potassium carbonate and 1.3 g (0.011 mol) of 2-dimethylaminoethyl chloride in 100 mL of ethyl acetate was stirred and heated at reflux for 2 hrs, then twice an additional 0.5 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 organic solution was separated, washed with brine, dried (MgSO4) and the solvent was removed under reduced pressure. The residue in acetone was treated with hydrogen chloride (anhydrous) and the crude hydrochloride salt after recrystallization from acetone afforded 4.0 g (80%) of rac.-cis-6-(acetyloxy)-6,7-dihydro-7-(4-methoxyphenyl)-4 -[2-(dimethylamino)ethyl]-3-phenyl-1,4-thiazepin-5(4H)-one hydrochloride, mp 125°-127°.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hrs
  3. temperatureThe mixture was heated
  4. temperatureat reflux for a total of 12 hrs
  5. customThe organic solution was separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. customthe solvent was removed under reduced pressure
  9. additionThe residue in acetone was treated with hydrogen chloride (anhydrous)
  10. customthe crude hydrochloride salt after recrystallization from acetone

Sources & evidence

ORD record
ord-c0c27565a56c4ee1abb5cb96974f3cd0
Source dataset
uspto-grants-1991_02
Patent number
US04992432

Reaction notes

Loading…