Triethylamine → Ammonia

HRID 346682Notes

Reaction equation

HRID 346682 reaction equation
Cl.Cl[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[NH:9]1[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(N(CC)CC)C>CC(C)CCO>[NH3:6].[N:6]1[CH:7]=[CH:8][C:3]([N:9]2[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 68163Hexahydro-1,4-diazepineHCID 818524-Chloropyridine hydrochloride

Product 2

HCID 222AmmoniaHCID 27605081-pyridin-4-yl-1,4-diazepane

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent2×

Procedure

A suspension of 4-chloropyridine hydrochloride (7.5 g) in 3-methyl-1-butanol (100 ml) was added dropwise to a refluxing solution of hexahydro-1,4-diazepine (10.0 g) and triethylamine (16.8 ml) in 3-methyl-1-butanol (300 ml). After addition the solution was refluxed for 18 hours. The solvent was removed in vacuo to give an oil. Purification by sinter-column chromatography on silica gel, eluting with dichloromethane containing an increasing proportion of methanol (2-5%) and a small amount of conc. aqueous ammonia, gave 1-(4-pyridyl)hexahydro-1,4-diazepine as a colourless oil which slowly crystallised on standing.

Workup

  1. additionAfter addition the solution
  2. temperaturewas refluxed for 18 hours
  3. customThe solvent was removed in vacuo
  4. customto give an oil
  5. customPurification by sinter-column chromatography on silica gel
  6. washeluting with dichloromethane containing an increasing proportion of methanol (2-5%)

Sources & evidence

ORD record
ord-3bbca0678af6482986eed40f4e42c5f6
Source dataset
uspto-grants-2007_02
Patent number
US07173025B1

Reaction notes

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