Ethylenediamine → HCID 13279663, compound

HRID 1730976Notes

Reaction equation

HRID 1730976 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11](O)=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([NH2:21])[CH2:19][NH2:20].[Li].[H-]>O>[C:2]1([CH:1]2[C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[CH2:11][NH:21][CH2:18][CH2:19][NH:20]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 3301EthylenediamineHCID 68132-Benzoylbenzoic AcidHCID 166653HydrideHCID 3028194Lithium

Product 1

HCID 13279663HCID 13279663, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 40 g. of the condensation product of o-benzoylbenzoic acid and ethylenediamine in small portions to a suspension of 15 g. of lithium aliminum hydride in 1500 ml. of anhydrous either with stirring. Reflux with stirring for 16 hours. Cool and add water carefully to decompose excess hydride. Separate the ether layer, dry over magnesium sulfate, and remove the solvent under reduced pressure to obtain 1,2,3,4,5,6-hexahydro-1-phenyl-2,5-benzodiazocine, m.p. 125° C. To prepare the dihydrochloride, dissolve the base in anhydrous ether and saturate with dry hydrogen chloride. Separate the precipitated solid, and recrystallize from ethanol to obtain 1,2,3,4,5,6-hexahydro-1-phenyl-2,5-benzodiazocine dihydrochloride, m.p. 297° C. (dec.).

Workup

  1. additionAdd 40 g
  2. temperatureReflux
  3. stirringwith stirring for 16 hours
  4. temperatureCool
  5. customSeparate the ether layer
  6. dry with materialdry over magnesium sulfate
  7. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-d008aeb10f514019afa0db2c74350996
Source dataset
uspto-grants-1976_11
Patent number
US03994920

Reaction notes

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