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Hydrochloric Acid → Indecainide Hydrochloride

HRID 1381329
Notes
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Reaction equation

HRID 1381329 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[ClH:5].C([BH3-])#N.[Na+].O[CH:11]1[NH:16][C:15](=[O:17])[C:14]2([C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:23]3[C:18]2=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:13][CH2:12]1>C(#N)C>[ClH:5].[C:15]([C:14]1([CH2:13][CH2:12][CH2:11][NH:4][CH:1]([CH3:3])[CH3:2])[C:29]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2)(=[O:17])[NH2:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6363IsopropylamineHCID 5003444Sodium cyanoborohydrideHCID 133680416'-hydroxyspiro(9H-fluorene-9,3'-piperidine)-2'-one

Product 1

HCID 52194Indecainide Hydrochloride

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

A solution of isopropylamine (45.0 ml) in acetonitrile (250 ml) was cooled to 10° C. and hydrogen chloride gas introduced into the solution keeping the temperature below 15° C. to pH 8.5±0.3. The resultant slurry was allowed to warm to room temperature and sodium cyanoborohydride (12.0 g) added in one portion and the pH readjusted to 8.5 if necessary. 6'-Hydroxyspiro-(9H-fluorene-9,3'-piperidine)-2'-one (30.0 g) was then added and the reaction mixture heated to reflux for 2 hours. The mixture was allowed to cool to room temperature and dilute hydrochloride acid added to pH 1-2 to destroy any excess cyanoborohydride. The acetonitrile was removed under reduced pressure and the residue basified with sodium hydroxide solution (pH 11) and extracted with dichloromethane (3×100 ml) and the combined organic layers washed with sodium hydroxide solution, dried with anhydrous sodium sulphate and evaporated to give the crystalline free amine.

Workup

  1. customthe temperature below 15° C.
  2. temperaturethe reaction mixture heated
  3. temperatureto reflux for 2 hours
  4. temperatureto cool to room temperature
  5. customto destroy any excess cyanoborohydride
  6. customThe acetonitrile was removed under reduced pressure
  7. extractionextracted with dichloromethane (3×100 ml)
  8. washthe combined organic layers washed with sodium hydroxide solution
  9. dry with materialdried with anhydrous sodium sulphate
  10. customevaporated

Sources & evidence

ORD record
ord-7ba56c5f9ec24926af888d1ecaa78dca
Source dataset
uspto-grants-1986_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04585894

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes