2-Chloro-N,N-dimethylethylamine → HCID 131716585, compound

HRID 1032637Notes

Reaction equation

HRID 1032637 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][C:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:8]([CH3:26])[NH:7][C:6]1=[O:27])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:34][N:35]([CH3:39])[CH2:36][CH2:37]Cl.[C:40]([OH:47])(=[O:46])/[CH:41]=[CH:42]/[C:43]([OH:45])=[O:44]>C(OCC)(=O)C.O.CC(C)=O>[C:40]([OH:47])(=[O:46])/[CH:41]=[CH:42]/[C:43]([OH:45])=[O:44].[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][C:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:8]([CH3:26])[N:7]([CH2:37][CH2:36][N:35]([CH3:39])[CH3:34])[C:6]1=[O:27])(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 79012-Chloro-N,N-dimethylethylamine2×HCID 11430Potassium CarbonateHCID 444972Fumaric AcidHCID 14855979HCID 14855979, compound

Product 1

HCID 131716585HCID 131716585, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.7 g (0.0044 mol) of cis-rac.-6-(acetyloxy)-6,7-dihydro-7-(4-methoxyphenyl)-3-methyl-2-phenyl-1,4-thiazepin-5(4H)-one, 0.7 g (0.005 mol) of powdered potassium carbonate and 0.6 g (0.0049 mol) of 2-dimethylaminoethyl chloride in 30 ml of ethyl acetate was stirred at reflux for 2 hours, then twice an additional 0.2 g of dimethylaminoethyl chloride was added at 2 hour intervals. The mixture was heated at reflux for a total of 12 hours, then cooled to room temperature and diluted with water. The organic solution was separated, washed with brine then dried (MgSO4) and the solvent was removed under reduced pressure. The residue was dissolved in acetone and passed through a 10 g silica gel pad which was washed with acetone (12×30 ml). The solvent was evaporated to give 1.8 g (0.039 mol) of crude base which was dissolved in acetone and 0.5 g (0.04 mol) of fumaric acid was added. The resulting crystals were collected to give 1.1 g (44%) cis-rac.-6-(acetyloxy)-6,7-dihydro-7-(4-methoxyphenyl)-3-methyl-4-[2-(dimethylamino)ethyl]-2-phenyl-1,4-thiazepin-5(4H)-one (E)-2-butenedioate, mp 176°-177°.

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureThe mixture was heated
  3. temperatureat reflux for a total of 12 hours
  4. customThe organic solution was separated
  5. washwashed with brine
  6. dry with materialthen dried (MgSO4)
  7. customthe solvent was removed under reduced pressure
  8. dissolutionThe residue was dissolved in acetone
  9. washwas washed with acetone (12×30 ml)
  10. customThe solvent was evaporated
  11. customto give 1.8 g (0.039 mol) of crude base which
  12. customThe resulting crystals were collected

Sources & evidence

ORD record
ord-dcae1f7dd6b04eebbd94af0942cb0a22
Source dataset
uspto-grants-1990_09
Patent number
US04959359

Reaction notes

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