Hydrochloric Acid → HCID 178426011, compound

HRID 49194Notes

Reaction equation

HRID 49194 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:24])=[C:6]([CH:8]2[CH2:17][C:16]3[N:15]=[CH:14][CH:13]=[C:12]([CH3:18])[C:11]=3[C:10](=[N:19][NH:20][C:21]([NH2:23])=[NH:22])[CH2:9]2)[CH:7]=1.[ClH:25]>C(O)C>[ClH:25].[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:24])=[C:6]([CH:8]2[CH2:17][C:16]3[N:15]=[CH:14][CH:13]=[C:12]([CH3:18])[C:11]=3[C:10](=[N:19][NH:20][C:21]([NH2:23])=[NH:22])[CH2:9]2)[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178426010HCID 178426010, compound

Product 1

HCID 178426011HCID 178426011, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (−)-7-(5-fluoro-2-methylphenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline (1.5 g) in ethanol (20 ml) was combined with concentrated hydrochloric acid (1.2 ml) and concentrated. The resultant crystal was recrystallized from a solvent mixture of ethanol and water to obtain (−)-7-(5-fluoro-2-methylphenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound E) (0.96 g, 99.3% ee). (This compound was proven to have an absolute configuration of an S form based in an X-ray crystal structure analysis.)

Workup

  1. concentrationconcentrated
  2. customThe resultant crystal was recrystallized from a solvent mixture of ethanol and water

Sources & evidence

ORD record
ord-3b086ec4c45d47b7a00711e6ac2619ae
Source dataset
uspto-grants-2004_03
Patent number
US06706732B1

Reaction notes

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