Hydrochloric Acid → 1-((6-chloropyridin-3-yl)methyl)-2,3,5,6,7,8-hexahydro-1H-5,8-epoxyimidazo[1,2-a]azepine-9-carbonitrile

HRID 1043523Notes

Reaction equation

HRID 1043523 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:13][CH2:12][NH:11][C:10]2=[CH:14][C:15]#[N:16])=[CH:4][CH:3]=1.[CH:17](=[O:22])[CH2:18][CH2:19][CH:20]=O.Cl>C(#N)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[C:10]3=[C:14]([C:15]#[N:16])[CH:20]4[O:22][CH:17]([N:11]3[CH2:12][CH2:13]2)[CH2:18][CH2:19]4)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12524ButanedialHCID 743284342-(1-((6-Chloropyridin-3-yl)methyl)imidazolidin-2-ylidene)acetonitrile

Product 1

HCID 866589441-((6-chloropyridin-3-yl)methyl)-2,3,5,6,7,8-hexahydro-1H-5,8-epoxyimidazo[1,2-a]azepine-9-carbonitrileYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 50 ml round bottom flask was added 1.17 g (0.005 mol) 2-(1-((6-chloropyridin-3-yl)methyl)imidazolidin-2-ylidene)acetonitrile, 30 ml dry acetonitrile and 0.860 g (0.01 mol) succinaldehyde and catalytic concentrated HCl. The reaction was stirred at r.t. and monitored by TLC. After completion, the mixture was evaporated to remove solvent and purified by column chromatography to afford final product as faint yellow powder with 66% yield.

Workup

  1. customAfter completion, the mixture was evaporated
  2. customto remove solvent
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-7129a57a4f2f46cd8d13d886b35a99f9
Source dataset
uspto-grants-2013_10
Patent number
US08563546B2

Reaction notes

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