Hydrochloric Acid → HCID 20382060, compound

HRID 1448134Notes

Reaction equation

HRID 1448134 reaction equation
N1CCCNC[CH2:2]1.N1CCNCC1.[N:14]1([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][C:22]=2[O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:20][CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.Cl>C=O.CO.C(O)=O>[CH3:2][N:17]1[CH2:18][CH2:19][CH2:20][N:14]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][C:22]=2[O:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:15][CH2:16]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 4837PiperazineHCID 68163Hexahydro-1,4-diazepineHCID 20382069HCID 20382069, compound

Product 1

HCID 20382060HCID 20382060, compound

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 712FormaldehydeSolventHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

By substituting 30 g of hexahydro-1H-1,4-diazepine for the piperazine in Example 1, the product is 4-(hexahydro-1H-1,4-diazepin-1-yl)-3-phenoxy pyridine, bp 143°-145° C./0.13 mm). Three and four tenths g of this material is dissolved in a mixture of 4.5 g 37% formalin and 2 ml of methanol and is treated with 6 g of 97-100% formic acid. The mixture is heated at 100° C. for 18 hours. The mixture is cooled, treated with an excess of dilute hydrochloric acid and concentrated in vacuo. The residue is shaken with 100 ml of toluene and excess dilute aqueous sodium hydroxide. The organic phase is dried, concentrated and distilled to give 4-(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)-3-phenoxypyridine; bp 130°-131° C./0.1 mm.

Workup

  1. temperatureThe mixture is cooled
  2. concentrationconcentrated in vacuo
  3. customThe organic phase is dried
  4. concentrationconcentrated
  5. distillationdistilled

Sources & evidence

ORD record
ord-2961c5e597154513b07b3964c153169a
Source dataset
uspto-grants-1979_12
Patent number
US04179563

Reaction notes

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