Hydrochloric Acid → HCID 20155177, compound

HRID 2413698Notes

Reaction equation

HRID 2413698 reaction equation
[NH:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][C:2]1=[O:11].Cl.NC1(CCC(O)=O)CCCCC1.[P:25]([OH:28])([OH:27])[OH:26].P(Cl)(Cl)Cl>O>[NH2:1][C:5]1([CH2:4][CH2:3][C:2]([OH:11])([P:25]([OH:28])(=[O:26])[OH:27])[P:25]([OH:28])(=[O:27])[OH:26])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

7

Reactant 5

HCID 313Hydrochloric Acid3×HCID 24387Phosphorus trichlorideHCID 107909Phosphorous acidHCID 2479941-Azaspiro(4.5)decan-2-oneHCID 20155191HCID 20155191, compound

Product 1

HCID 20155177HCID 20155177, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

19.1 g. 1-Aza-spiro(4,5)decan-2-one (prepared as described in J. Org. Chem., 22, 832) are boiled for 90 hours in 190 ml. concentrated hydrochloric acid. After cooling, the reaction mixture is filtered and evaporated and the residue is reprecipitated with methanol/diethyl ether. There are obtained 17.5 g. (68% of theory) of the hydrochloride of 3-(1-aminocyclohexyl)-propionic acid; m.p. 183° C. sinters; 188°-192° C. melts with decomposition. 7 g. thereof are mixed with 5.5 g. phosphorous acid and, after melting at 80° C., mixed dropwise with 5.9 ml. phosphorus trichloride. After stirring for 8 hours at 80° C., 43 ml. 6N hydrochloric acid are added thereto, the temperature is increased to 100° C. and stirring continued for a further 8 hours. The yellowish suspension is then filtered hot, the filtrate is evaporated and the residue, a colourless oil, is stirred into 2 liters of acetone. The precipitate obtained is filtered off with suction and washed with acetone and diethyl ether. There are obtained 4.6 g. (43% of theory) of product which are dissolved in a little water. Purification takes place by fractionation on an Amberlite IR-120 column (H+ form). The individual fractions are tested electrophoretically for purity. After combining the pure fractions, the aqueous solution is again evaporated and again precipitated with acetone. There are obtained 2.9 g. (27% of theory) of white crystals; m.p. 143° C. sinters, 155°-158° C. foaming up; Mrel =0.29.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture is filtered
  3. customevaporated
  4. customthe residue is reprecipitated with methanol/diethyl ether
  5. customThere are obtained 17.5 g
  6. custom188°-192° C.
  7. additionthereof are mixed with 5.5 g
  8. temperaturethe temperature is increased to 100° C.
  9. stirringstirring
  10. waitcontinued for a further 8 hours
  11. filtrationThe yellowish suspension is then filtered hot
  12. customthe filtrate is evaporated
  13. stirringthe residue, a colourless oil, is stirred into 2 liters of acetone
  14. customThe precipitate obtained
  15. filtrationis filtered off with suction
  16. washwashed with acetone and diethyl ether
  17. customThere are obtained 4.6 g
  18. customPurification
  19. customthe aqueous solution is again evaporated
  20. customagain precipitated with acetone
  21. customThere are obtained 2.9 g
  22. customm.p. 143° C. sinters, 155°-158° C.

Sources & evidence

ORD record
ord-8dfc7888e4c6429d8b3164574728fd35
Source dataset
uspto-grants-1988_01
Patent number
US04719203

Reaction notes

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