2-Chloro-N,N-dimethylethylamine → HCID 14855981, compound

HRID 1032639Notes

Reaction equation

HRID 1032639 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(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][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

6

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamine2×HCID 11430Potassium CarbonateHCID 14855978HCID 14855978, compound

Product 1

HCID 14855981HCID 14855981, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2.3 g (0.006 mol) of trans-rac.-6-(acetyl-oxy)-6,7-dihydro-7-(4-methoxyphenyl)-3-methyl-2-phenyl-1,4-thiazepin-5(4H)-one, 1.0 g (0.0072 mol) of powdered potassium carbonate, and 0.8 g (0.0066 mol) of 2-dimethylaminoethyl chloride in 50 ml of ethyl acetate was stirred and heated at reflux for 2 hours, then twice an additional 0.3 g of dimethylaminoethyl chloride was added at 2 hour intervals. The mixture was heated at reflux for a total of 2 hours, then cooled to room temperature and diluted with water. The organic phase was separated, washed with brine and dried (MgSO4) and the solvent was removed under reduced pressure. The residue was crystallized from ether to give 1.7 g (70%) of trans-rac.-6-(acetyloxy)-6,7-dihydro-7-(4-methoxyphenyl)-3-methyl-4-[2-(dimethylamino)-ethyl]-2-phenyl-1,4-thiazepin-5(4H)-one, mp 119°-120°.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. temperatureThe mixture was heated
  4. temperatureat reflux for a total of 2 hours
  5. customThe organic phase was separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was crystallized from ether

Sources & evidence

ORD record
ord-1d318fca6b284b9b81479c731df48b50
Source dataset
uspto-grants-1990_09
Patent number
US04959359

Reaction notes

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