Hydrochloric Acid → HCID 178479267, compound

HRID 979889Notes

Reaction equation

HRID 979889 reaction equation
C(O)C.[NH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH2:15][CH2:14][NH:13][C:12]2=[O:16])[CH2:7][CH2:6]1.[ClH:17]>C(OCC)(=O)C>[ClH:17].[NH2:4][C@@H:5]1[CH2:6][CH2:7][C@H:8]([N:11]2[CH2:15][CH2:14][NH:13][C:12]2=[O:16])[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 13755489HCID 13755489, compound

Product 1

HCID 178479267HCID 178479267, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 9500 ml of anhydrous ethyl alcohol and 2323 g of 1-(4-aminocyclohexyl)-2-imidazolidinone is heated with mixing to effect solution. The solution is cooled to room temperaure and 3200 ml of a saturated solution of anhydrous hydrogen chloride gas in ethyl acetate is added to pH 1. The temperature of the mixture rises to 60° and the product crystallizes. The mixture is cooled to 10°. The crude product is filtered off, washed with 3500 ml of anhydrous ethyl alcohol and dried at 50°-60° in vacuo for 2 days. The crude hydrochloride salt is recrystallized twice from anhydrous methanol-ethyl ether (ca 1:1) to give cis 1-(4-aminocyclohexyl)-2-imidazolidinone monohydrochloride, m.p. 327°-8°.

Workup

  1. temperatureis heated
  2. additionwith mixing
  3. additionis added to pH 1
  4. customrises to 60°
  5. customthe product crystallizes
  6. temperatureThe mixture is cooled to 10°
  7. filtrationThe crude product is filtered off
  8. washwashed with 3500 ml of anhydrous ethyl alcohol
  9. customdried at 50°-60° in vacuo for 2 days
  10. customThe crude hydrochloride salt is recrystallized twice from anhydrous methanol-ethyl ether (ca 1:1)

Sources & evidence

ORD record
ord-cac256ff9db44d129578dd412860a1cc
Source dataset
uspto-grants-1987_01
Patent number
US04634713

Reaction notes

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