3-Chloropropyl(diethyl)amine → N,N-diethyl-N'-{dibenzo[b,e]thiepin-11(6H)-ylidene}-1,3-propanediamine

HRID 1287924Notes

Reaction equation

HRID 1287924 reaction equation
[Na].[CH:2]1[C:12]2[C:11](=[N:13]O)[C:10]3[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=3[CH2:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:19]([N:21]([CH2:26][CH3:27])[CH2:22][CH2:23][CH2:24]Cl)[CH3:20]>C(O)C>[CH2:19]([N:21]([CH2:26][CH3:27])[CH2:22][CH2:23][CH2:24][N:13]=[C:11]1[C:10]2[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=2[CH2:8][S:7][C:6]2[CH:5]=[CH:4][CH:3]=[CH:2][C:12]1=2)[CH3:20]

Participants

5

Reactant 3

HCID 669183-Chloropropyl(diethyl)amineHCID 5360545SodiumHCID 73794634Dibenzo[b,e]thiepin-11(6H)-one, oxime

Product 1

HCID 21507028N,N-diethyl-N'-{dibenzo[b,e]thiepin-11(6H)-ylidene}-1,3-propanediamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

1.65 G. of sodium in 60 ml. of absolute ethanol are treated dropwise with 11.4 g. of dibenzo[b,e]thiepin-11(6H)-one-oxime in 60 ml. of absolute ethanol. The mixture is stirred at 50° C. for 3 hours and then cooled to 5°-10° C. The mixture is then treated dropwise with 15.3 g. of 3-diethylamino-propyl chloride, stirred at 50° C. for 16 hours and subsequently evaporated under reduced pressure. The residue is dissolved in chloroform, washed with water, dried over sodium sulfate and evaporated under reduced pressure. The resulting residue is purified by chromatography over aluminum oxide using chloroform for the elution. A by-product is first eluted and there is subsequently eluted the desired N,N-diethyl-N'-{dibenzo[b,e]thiepin-11(6H)-ylidene}-1,3-propanediamine-N'-oxide which is used directly in the process described in the first paragraph of this Example.

Workup

  1. temperaturecooled to 5°-10° C
  2. additionThe mixture is then treated dropwise with 15.3 g
  3. customsubsequently evaporated under reduced pressure
  4. dissolutionThe residue is dissolved in chloroform
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe resulting residue is purified by chromatography over aluminum oxide
  9. washfor the elution
  10. washA by-product is first eluted
  11. washthere is subsequently eluted the desired N,N-diethyl-N'-{dibenzo[b,e]thiepin-11(6H)-ylidene}-1,3-propanediamine-N'-oxide which

Sources & evidence

ORD record
ord-1074b8be7c624124b9eb397a9f02875d
Source dataset
uspto-grants-1976_10
Patent number
US03985895

Reaction notes

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