Hydrochloric Acid → HCID 131726642, compound

HRID 1180510Notes

Reaction equation

HRID 1180510 reaction equation
N[C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.N([O-])=O.[Na+].[OH-].[Na+].[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25].[ClH:29]>>[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25].[Cl:29][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 444972Fumaric AcidHCID 22053546HCID 22053546, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 131726642HCID 131726642, compound

Procedure

1-(6-Amino-3-pyridyl)-homopiperazine (96 mg, 0.5 mmol) was solyed in conc. hydrochloric acid (2.0 ml). Sodium nitrite (45 mg, 0.65 mmol) was added at 0° C. The mixture was allowed to reach room-temperature and was stirred overnight. The mixture was poured out on water (20 ml) and was refluxed for 10 minutes. The mixture was made alkaline by adding aqueous sodium hydroxide (1.0 ml, 4 M). The mixture was extracted with ethyl acetate (3×10 ml). The product was isolated as an oil. Yield 50 mg (47%). The free base was converted to the corresponding fumaric acid salt. Mp. 165-167° C.

Workup

  1. additionThe mixture was poured out on water (20 ml)
  2. temperaturewas refluxed for 10 minutes
  3. extractionThe mixture was extracted with ethyl acetate (3×10 ml)
  4. customThe product was isolated as an oil

Sources & evidence

ORD record
ord-75977881de144c2fab844cd167529e1b
Source dataset
uspto-grants-2007_10
Patent number
US07282494B2

Reaction notes

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