Morpholine, hydrochloride (1:1) → N'-(N'-cyclopropylcarbamimidoyl)morpholine-4-carboximidamide;hydrochloride

HRID 2226382Notes

Reaction equation

HRID 2226382 reaction equation
[C:1]([NH:3][C:4]([NH:6][CH:7]1[CH2:9][CH2:8]1)=[NH:5])#[N:2].[ClH:10].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>C(O)(C)C>[ClH:10].[NH:5]=[C:4]([NH:6][CH:7]1[CH2:9][CH2:8]1)[NH:3][C:1]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[NH:2]

Participants

4

Reactant 2

HCID 197884Morpholine, hydrochloride (1:1)HCID 178512341HCID 178512341, compound

Product 1

HCID 178479355N'-(N'-cyclopropylcarbamimidoyl)morpholine-4-carboximidamide;hydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 4.0 g (32.3 mmoles) of N-cyano-N'-cyclopropylguanidine and 3.98 g (32.3 mmoles) of morpholine hydrochloride is heated at 160° C. under a nitrogen atmosphere for 2 and a half hours. The solid mass obtained is dissolved in 200 ml of boiling isopropyl alcohol. The mixture is filtered hot and the filtrate is concentrated until a solid suspension appears. The mixture is then cooled to room temperature and 200 ml of diethyl ether are added. The reaction product crystallizes. It is filtered, washed with diethyl ether and dried. 6.8 g of N-[imino(cyclopropylamino)methyl]-4-morpholinecarboximidamide hydrochloride are obtained.

Workup

  1. customThe solid mass obtained
  2. filtrationThe mixture is filtered hot
  3. concentrationthe filtrate is concentrated until a solid suspension
  4. temperatureThe mixture is then cooled to room temperature
  5. addition200 ml of diethyl ether are added
  6. customThe reaction product crystallizes
  7. filtrationIt is filtered
  8. washwashed with diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-d673e40ee550411ca845bf7918dfaff3
Source dataset
uspto-grants-1994_09
Patent number
US05348956

Reaction notes

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