Dimethylcarbamoyl Chloride → HCID 70579501, compound

HRID 894466Notes

Reaction equation

HRID 894466 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:21]([OH:22])=[CH:20][C:7]2[C@H:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:9][N:10]([CH3:13])[CH2:11][CH2:12][C:6]=2[CH:5]=1.[CH3:23][N:24]([CH3:28])[C:25](Cl)=[O:26]>C(COC)OC>[ClH:3].[Cl:3][C:4]1[C:21]([O:22][C:25]([N:24]([CH3:28])[CH3:23])=[O:26])=[CH:20][C:7]2[C@H:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:9][N:10]([CH3:13])[CH2:11][CH2:12][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 6603800(5S)-8-Chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepin-7-ol

Product 1

HCID 70579501HCID 70579501, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Add in small portions with stirring, 360 mg of sodium hydride (50% in mineral oil) to a suspension of 2.16 g (0.0075 moles) of (S)-7-chloro-8-hydroxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine (as obtained in step E of Example 1) in 35 ml of anhydrous dimethoxyethane and stir until the evolution of gas ceases. Add dropwise a solution of 0.75 ml of dimethylcarbamyl chloride in 5 ml of anhydrous dimethoxyethane. Stir for 36 hours at room temperature and concentrate to dryness; dissolve the residue in 50 ml of ethyl ether and filter to remove the solid. Wash the filtrate twice with 30 ml of 0.5 N sodium hydroxide, dry the ether layer over anhydrous sodium sulfate, and precipitate (S)-7-chloro-8-dimethylaminocarbonyloxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride with 1 N ethereal hydrogen chloride. Obtain an analytical sample by crystallization from 2-propanol, m.p. 261°-263° C. [α]D26 =+23.1° (c=1, dimethylformamide).

Workup

  1. additionAdd in small portions
  2. stirringstir until the evolution of gas ceases
  3. stirringStir for 36 hours at room temperature
  4. concentrationconcentrate to dryness
  5. dissolutiondissolve the residue in 50 ml of ethyl ether
  6. filtrationfilter
  7. customto remove the solid
  8. washWash the filtrate twice with 30 ml of 0.5 N sodium hydroxide
  9. dry with materialdry the ether layer over anhydrous sodium sulfate, and precipitate (S)-7-chloro-8-dimethylaminocarbonyloxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride with 1 N ethereal hydrogen chloride
  10. customObtain an analytical sample
  11. customby crystallization from 2-propanol, m.p. 261°-263° C. [α]D26 =+23.1° (c=1, dimethylformamide)

Sources & evidence

ORD record
ord-0e995a4648754e029cf2c726ee6c2fb3
Source dataset
uspto-grants-1981_08
Patent number
US04284555

Reaction notes

Loading…