1-Chloro-2-(diethylamine)ethane hydrochloride → HCID 21455232, compound

HRID 1606441Notes

Reaction equation

HRID 1606441 reaction equation
[H-].[Na+].Cl.[CH2:4]([N:6]([CH2:9][CH2:10]Cl)[CH2:7][CH3:8])[CH3:5].[CH3:12][N:13]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[NH:17][C:16](=[O:24])[C:15]2=[CH:25][S:26][CH:27]=[C:14]12>CN(C)C=O>[CH2:4]([N:6]([CH2:7][CH3:8])[CH2:9][CH2:10][N:17]1[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:13]([CH3:12])[C:14]2=[CH:27][S:26][CH:25]=[C:15]2[C:16]1=[O:24])[CH3:5]

Participants

5

Reactant 3

HCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 24758Sodium hydrideHCID 125216424,9-Dihydro-4-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 21455232HCID 21455232, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.31 g. of 55% sodium hydride-mineral oil dispersion and 0.60 g. of diethylaminoethylchloride hydrochloride in 25 ml. of dry dimethylformamide is stirred at room temperature for 0.5 hours. To the mixture is added 0.4 g. of 4,9-dihydro-4-methyl-10H-thieno[3,4-b] [1,5]benzodiazepin-10-one and stirring is continued for 18 hours. The reaction mixture is cooled, quenched with water and extracted with chloroform. The chloroform extracts are concentrated under reduced pressure to an oil, which is chromatographed on silica gel preparative thin layer chromatographic (tlc) plates using 10:1 benzene:methanol as eluent. The oily product is crystallized from hexane to give white crystals, m.p. 92°-93°C.

Workup

  1. additionA mixture of 0.31 g
  2. additionTo the mixture is added 0.4 g
  3. temperatureThe reaction mixture is cooled
  4. customquenched with water
  5. extractionextracted with chloroform
  6. concentrationThe chloroform extracts are concentrated under reduced pressure to an oil, which
  7. customis chromatographed on silica gel preparative thin layer chromatographic (tlc) plates
  8. customThe oily product is crystallized from hexane
  9. customto give white crystals, m.p. 92°-93°C.

Sources & evidence

ORD record
ord-baa32e22553849e194955e189ab9e46b
Source dataset
uspto-grants-1976_04
Patent number
US03953430

Reaction notes

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