2-Chloro-N,N-dimethylethylamine → HCID 131715616, compound

HRID 580386Notes

Reaction equation

HRID 580386 reaction equation
[H-].[Na+].CCCCCC.[Cl:9][C:10]1[CH:11]=[CH:12][C:13]2[NH:19][C:18](=[O:20])[CH:17]([CH2:21][CH3:22])[CH:16]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[CH2:15][C:14]=2[CH:31]=1.[CH3:32][N:33]([CH2:35][CH2:36]Cl)[CH3:34]>CN(C)C=O>[ClH:9].[Cl:9][C:10]1[CH:11]=[CH:12][C:13]2[N:19]([CH2:36][CH2:35][N:33]([CH3:34])[CH3:32])[C:18](=[O:20])[C@@H:17]([CH2:21][CH3:22])[C@@H:16]([C:23]3[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=3)[CH2:15][C:14]=2[CH:31]=1

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 20135074HCID 20135074, compoundHCID 86738843HCID 86738843, compound

Product 1

HCID 131715616HCID 131715616, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a slurry of prewashed (hexane) sodium hydride (~50% in mineral oil) (0.064 g; 1.34 mmole; 1.2 eq.) in dry dimethylformamide (10 ml) was added 7-chloro-3-ethyl-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one (370 mg; 1.12 mmole). After stirring the mixture at 25° C. for 1 hour, 3.2 ml (5.6 mmole) of 1.7N N,N-dimethyl-2-chloroethylamine (in toluene) was added, and the solution was heated at 80° C. for 24 hours. The reaction was quenched with 1N hydrochloric acid, made basic with 50% sodium hydroxide solution, extracted with ethyl acetate (two times) and dried (magnesium sulfate). After solvent removal, 0.49 g of a brown oil remained. This crude product was flash chromatographed (silica gel/3:1-hexane:ethyl acetate, followed by 2:1-hexane: ethyl acetate, followed by 1:1-hexane: ethyl acetate, followed by ethyl acetate). Those fractions which contained the cis amine product were dissolved into ether. The salt was precipitated out by the dropwise addition of hydrogen chloride saturated ether solution. The resultant white solid was collected by suction-filtration, yielding 200 mg. The lower Rf trans isomer of the title compound was likewise obtained (10 mg) as well as a cis-trans mixture (50 mg), and unreacted starting material (40 mg).

Workup

  1. temperaturethe solution was heated at 80° C. for 24 hours
  2. customThe reaction was quenched with 1N hydrochloric acid
  3. extractionextracted with ethyl acetate (two times)
  4. dry with materialdried (magnesium sulfate)
  5. customAfter solvent removal, 0.49 g of a brown oil
  6. customchromatographed (silica gel/3:1-hexane:ethyl acetate, followed by 2:1-hexane: ethyl acetate, followed by 1:1-hexane: ethyl acetate, followed by ethyl acetate)
  7. dissolutionwere dissolved into ether
  8. customThe salt was precipitated out by the dropwise addition of hydrogen chloride saturated ether solution
  9. filtrationThe resultant white solid was collected by suction-filtration
  10. customyielding 200 mg

Sources & evidence

ORD record
ord-9079ac7630f348ce848a29413a2a1125
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

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