Tetrafluoro-m-phenylenediamine dihydrochloride → 4-[2-(4,5,6,7-tetrahydro-1H-1,3-diazepin-2-yl)ethyl]piperidine

HRID 364719Notes

Reaction equation

HRID 364719 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]2[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]=2)=[CH:3][CH:2]=1.[H][H].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>C(O)C.O=[Pt]=O>[NH:15]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]=[C:9]1[CH2:8][CH2:7][CH:4]1[CH2:3][CH2:2][NH:1][CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 132811944,5,6,7-tetrahydro-2[2-(4-pyridyl)ethyl]-1H-1,3-diazepineHCID 178418361HCID 178418361, compound

Product 1

HCID 202397524-[2-(4,5,6,7-tetrahydro-1H-1,3-diazepin-2-yl)ethyl]piperidineYield 76.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

The 4,5,6,7-tetrahydro-2[2-(4-pyridyl)ethyl]-1H-1,3-diazepine (1.9 g, 0.009M) and PtO2 (0.25 g) in ethanol (20 ml) and 2NHCl (15 ml) was reduced at 45 psig of hydrogen. After the hydrogenation, the solvent was removed and the residue was crystallized from ethanol-ether to give 1.5 g of 4-[2-(4,5,6,7-tetrahydro-1H-1,3-diazepin-2-yl)ethyl]piperidine (60% yield) as dihydrochloride salt.

Workup

  1. customAfter the hydrogenation, the solvent was removed
  2. customthe residue was crystallized from ethanol-ether

Sources & evidence

ORD record
ord-d1a500a4f87a4b6a9ccadbf854f44448
Source dataset
uspto-grants-1986_08
Patent number
US04605744

Reaction notes

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