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

HRID 485794Notes

Reaction equation

HRID 485794 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 2 NHCl (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-37838a1459ba4a5c8a141ba0bfc2e5d7
Source dataset
uspto-grants-1985_08
Patent number
US04537969

Reaction notes

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