Hydrochloric Acid → HCID 178442812, compound

HRID 1437077Notes

Reaction equation

HRID 1437077 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[ClH:14].Cl.[CH2:16]([NH:23][C:24]([NH:26][C:27]([NH2:29])=[NH:28])=[NH:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[ClH:14].[NH2:29][C:27]1[NH:26][C:24]([NH:23][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:25][CH:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[N:28]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8194DodecanalHCID 178479484HCID 178479484, compound

Product 1

HCID 178442812HCID 178442812, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

160 ml of ethanol, 13.0 g (70.5 mmol) of 1-dodecanal and 1.5 ml of concentrated hydrochloric acid were added to 8.0 g (35.1 mmol) of N1-benzyl-biguanide hydrochloride. The mixture was refluxed for 16 hours, and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography, and the first main fraction eluted with a mixture of chloroform and methanol (9:1.5) was recrystallized from 80% aqueous ethanol to obtain 3.1 g of colorless crystals (1) having a melting point of 152 to 155° C. The second main fraction was recrystallized from 80% aqueous ethanol to obtain 0.9 g of colorless crystals (2) having a melting point of 153 to 156° C.

Workup

  1. temperatureThe mixture was refluxed for 16 hours
  2. concentrationconcentrated under reduced pressure
  3. customto remove the solvent
  4. customThe residue was purified by silica gel column chromatography
  5. washthe first main fraction eluted with a mixture of chloroform and methanol (9:1.5)
  6. customwas recrystallized from 80% aqueous ethanol

Sources & evidence

ORD record
ord-9a872b49286f47f68653ef67d22fad4c
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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