Hydrochloric Acid → 1-(Aminomethyl)cyclohexan-1-amine dihydrochloride

HRID 44735Notes

Reaction equation

HRID 44735 reaction equation
[NH2:1][C:2]1([C:8]#[N:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[ClH:10]>C(O)C.[Pt]=O>[ClH:10].[ClH:10].[NH2:9][CH2:8][C:2]1([NH2:1])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 796351-Aminocyclohexanecarbonitrile

Product 1

HCID 175611601-(Aminomethyl)cyclohexan-1-amine dihydrochlorideYield 89%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent2×

Procedure

A mixture of 1-aminocyclohexanecarbonitrile (48.5 g, 391 mmol) and platinum oxide (5.0 g) in 4.2 M HCl in ethanol (200 mL) and 2.7 M HCl in ethanol (300 mL) was hydrogenated at 50 psi (3.4×105 Pa) for 20 h on a Parr apparatus. The reaction mixture was filtered through CELITE filter agent and the filtrate was concentrated to yield a clear oil. The oil was triturated with isopropanol to yield a white solid that was isolated by filtration, washed with ether, and dried to provide 1-(aminomethyl)cyclohexanamine dihydrochloride (70.0 g, 89%).

Workup

  1. filtrationThe reaction mixture was filtered through CELITE
  2. filtrationfilter agent
  3. concentrationthe filtrate was concentrated
  4. customto yield a clear oil
  5. customThe oil was triturated with isopropanol
  6. customto yield a white solid
  7. customthat was isolated by filtration
  8. washwashed with ether
  9. customdried

Sources & evidence

ORD record
ord-f6312d4939fb46a2b519de98282f6e3e
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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