Cyclopropylamine → HCID 178512231, compound

HRID 1788635Notes

Reaction equation

HRID 1788635 reaction equation
[C:1]([N:3]=[C:4](SC)[NH:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7]1)#[N:2].[CH:18]1([NH2:21])[CH2:20][CH2:19]1>C(O)C>[C:1]([N:3]=[C:4]([NH:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7]1)[NH:21][CH:18]1[CH2:20][CH2:19]1)#[N:2]

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 178503884HCID 178503884, compound

Product 1

HCID 178512231HCID 178512231, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 24.6 g of N'-cyano-N-(1,2,3,4-tetrahydro-1-naphthyl)-S-methylisothiourea and 25.0 g of cyclopropylamine in 250 ml of ethanol was heated at reflux with stirring for ca. 120 hours. The solvent was then removed by evaporation in vacuo. The residual oil was dissolved in a mixture of hot isopropyl acetate and ethanol, and the solution was allowed to stand in the refrigerator overnight to give the partially-purified product as a white, crystalline solid. A further quantity of the crude product was obtained by the concentration and subsequent cooling of the mother liquor. Recrystallization from isopropyl acetate, containing a small amount of ethanol, gave N"-cyano-N-cyclopropyl-N'-(1,2,3,4-tetrahydro-1-naphthyl)guanidine as 7.75 g of a white, crystalline solid, mp 170.5°-171.5° C.

Workup

  1. temperatureat reflux
  2. customThe solvent was then removed by evaporation in vacuo
  3. dissolutionThe residual oil was dissolved in a mixture of hot isopropyl acetate and ethanol
  4. customto stand in the refrigerator overnight
  5. customto give the partially-purified product as a white, crystalline solid
  6. customA further quantity of the crude product was obtained by the concentration
  7. temperaturesubsequent cooling of the mother liquor
  8. customRecrystallization from isopropyl acetate
  9. additioncontaining a small amount of ethanol

Sources & evidence

ORD record
ord-204270000ad042b79f64aead2300a0f3
Source dataset
uspto-grants-1987_08
Patent number
US04684398

Reaction notes

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